Publications by authors named "Shimei Jiang"

34 Publications

Tuning Organic Microcrystal Morphologies through Crystal Engineering Strategies toward Anisotropic Optical Waveguide.

J Phys Chem Lett 2021 May 10;12(19):4585-4592. Epub 2021 May 10.

Engineering Research Center of Organic and Polymer Optoelectronic Materials, Ministry of Education, State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, P. R. China.

The construction of organic optoelectronic materials with desirable size and morphology remains a challenge now. Crystal engineering strategies (polymorphs and cocrystals) provide convenience for tailoring molecular packing and further controlling the growth morphology and photofunctionality of materials. Herein, we prepare polymorphic 2D plate crystals and 3D microhelixes by assembly of a cyanostilbene derivative (2-(3',5'-bis(trifluoromethyl)-biphenyl-4-yl)-3-(4-(pyridin-4-yl)phenyl)acrylonitrile, CF-CN-Py). The former emits blue emission, while the latter emits green emission. Different crystallization environments contribute to the adjustable morphologies. Then, novel cocrystals are fabricated with the introduction of 1,4-diiodotetrafluorobenzene (FDIB) to CF-CN-Py. Both molecular conformation and packing are totally changed in the cocrystal system. Such cocrystal displays a 1D sky-blue emissive rod shape on account of a long-range ordered π-stacking of molecules. In addition, the 2D plate crystal and 1D rod cocrystal are further applied to optical waveguides. In the plate crystal, a packing of transition dipole moment (μ) inclined to the upper surface leads to an anisotropic optical waveguide. In the cocrystal, owing to the nearly horizontal μ orientation, the cocrystal exhibits light propagation along the primary growth direction and a low optical loss coefficient. The present study supplies an effective way to construct materials with controlled morphology and optical waveguide.
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http://dx.doi.org/10.1021/acs.jpclett.1c00769DOI Listing
May 2021

White-light-emitting hydrogels with self-healing properties and adjustable emission colors.

J Colloid Interface Sci 2021 Jan 25;582(Pt B):825-833. Epub 2020 Aug 25.

Engineering Research Center of Organic and Polymer Optoelectronic Materials, Ministry of Education, College of Chemistry, Jilin University, Changchun 130012, PR China; State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, PR China. Electronic address:

White-light-emitting soft materials with self-healing properties show extensive applications in many fields. Herein, a novel self-healing hydrogel is successfully fabricated using oxidized dextran (Odex) and dithiodipropionate dihydrazide (TPH). Carbon dots (CDs), Riboflavin (Ri) and Rhodamine B (RhB) are incorporated into the gel matrix to produce white light emission through fluorescence resonance energy transfer (FRET) process, thus achieving excellent Commission Internationale de L'eclairage (CIE) coordinate value of (0.30, 0.33). The emission colors can be easily tuned via changing proportions of three emitters or the excitation wavelength. When the hydrogels are coated on an ultraviolet light-emitting diodes (UV LED), the hydrogel coating converts UV light to white light and repairs itself in 20 h while a hole is dug from it. Thanks to reversible exchanging reactions of acylhydrazone and disulfide bonds in hydrogel networks, the hydrogel coating exhibits perfect self-healing property in a wide range of pH (from 5 to 9 except for 7). The excellent emission and self-healing properties of hydrogels have great value in practical applications.
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http://dx.doi.org/10.1016/j.jcis.2020.08.080DOI Listing
January 2021

Multi-color tunable circularly polarized luminescence in one single AIE system.

Chem Sci 2020 Jan 15;11(8):2169-2174. Epub 2020 Jan 15.

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University Changchun 130012 P. R. China

Circularly polarized luminescence (CPL) materials with a large luminescence dissymmetry factor ( ) and multi-color properties are very attractive. While multi-color tunable CPL can be realized by different organic dyes, the challenge of realizing both a higher and multiple colors using a single component remains. Here, we design an aggregation-induced emission (AIE) fluorophore, which is a pyridine functionalized cyanostilbene attached to a chiral unit, and realize multi-color tunable CPL with a high . The compound can self-assemble into a nanohelix and form both gel and xerogel films, exhibiting blue CPL with large values of -3.0 × 10 and -1.7 × 10, respectively. With the assistance of pyridine protonation, the xerogel films exhibit red-shifted CPL signals from 480 nm to 530 nm, covering from blue green and yellow to orange. Additionally, the remains constant during the process. This work paves a simple and convenient way to construct multi-color tunable CPL materials using a single molecule.
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http://dx.doi.org/10.1039/c9sc05643bDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8150103PMC
January 2020

Tunable morphologies and emission of photosensitive supramolecular self-assemblies through positional and trans-cis isomerization.

Nanoscale 2020 Jan;12(3):2071-2080

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, 2699 Qianjin Avenue, Changchun 130012, P. R. China.

Cyanostilbene units are widely attractive as photoresponsive supramolecular building blocks whose structures and emission can be modulated by trans-cis isomerization. Generally, the change of properties is related to the molecular structure of cyanostilbene, which is still unpredictable and needs to be explored. Herein, two benzene-1,3,5-tricarboxamide (BTA) based cyanostilbene derivatives with different cyano positions have been designed to investigate the emission as well as structural changes during the trans-cis photoisomerization process in monomer and aggregation states, respectively. In the monomer state, the derivative with cyano groups at the outer position, β-BTTPA, exhibits obvious emission enhancement upon UV irradiation, while the other derivative (α-BTTPA) shows emission quenching. In addition, upon the formation of aggregates, β-BTTPA forms nano-level fibers with blue-green emission, but α-BTTPA forms micron-level flat ribbons with blue emission. More importantly, also driven by the trans-cis photoisomerization, the self-assemblies show morphological transitions (ribbons/fibers to spheres) due to the fact that the equilibrium of the system is broken by the photoreactions. Such changes further contribute to emission switching as well as enhanced hydrophobic properties.
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http://dx.doi.org/10.1039/c9nr09155fDOI Listing
January 2020

Selective Cu(ii) sensing by a versatile AIE cyanostilbene-based gel system.

Soft Matter 2019 Aug 16;15(30):6145-6150. Epub 2019 Jul 16.

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, 2699 Qianjin Avenue, Changchun, 130012, P. R. China.

Cyanostilbene-based derivatives 1-3 were designed, synthesized and fully characterized. By screening their gelating abilities, we observed that the subtle difference in the position of the pyridine nitrogen greatly affected the resulting fluorescence and gelation properties. Notably, 1 was found to be a versatile ambidextrous gelator capable of forming organo-, hydro-, and Cu(ii) specific metallogels. Furthermore, a rare organogel-to-metallogel transformation at room temperature was also observed upon exposure of the 1-DMSO/HO gel to aqueous Cu(ii). This process, accompanied by colour and fluorescence changes, provides an effective strategy for the preparation of novel sensing soft materials.
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http://dx.doi.org/10.1039/c9sm00955hDOI Listing
August 2019

2-Phenyl-3-(-aminophenyl) Acrylonitrile: A Reactive Matrix for Sensitive and Selective Analysis of Glycans by MALDI-MS.

Anal Chem 2019 07 3;91(14):8801-8807. Epub 2019 Jul 3.

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry , Jilin University , Changchun 130012 , China.

Analysis of glycans by matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) is usually limited by the intrinsically low abundance and low ionization efficiency of glycans. Aiming to enhance the ionization efficiency of glycans and simplify the sample preparation procedure during MALDI-MS analysis, we reported herein a novel reactive matrix, 2-phenyl-3-(-aminophenyl) acrylonitrile (PAPAN), for sensitive and selective detection of glycans. PAPAN is a derivative of α-cyanocinnamic acid, which possesses high ionization efficiency in MALDI-MS. The PAPAN can react with the terminal aldehyde of glycans and thereby enable the significant enhancement of ionization efficiency of glycans. As a result, using PAPAN as a reactive matrix, the detection sensitivity for glycans was improved 100-fold compared with that using 2,5-dihydroxybenzoic acid (DHB) as the matrix. Meanwhile, the ionization of peptides can be significantly suppressed using PAPAN as the matrix, which allowed the selective detection of -glycans from a deglycosylated tryptic digest of glycoprotein without any prepurification. Moreover, the PAPAN matrix also endowed the analysis of glycans with enhanced fragmentation during MS/MS analysis, which could facilitate glycan structure interpretation. Finally, PAPAN was successfully used for the analysis of -glycome in human serum. Thus, a simple, sensitive, and selective method for the analysis of glycans has been achieved by using a novel reactive matrix, PAPAN.
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http://dx.doi.org/10.1021/acs.analchem.9b01434DOI Listing
July 2019

Highly Ordered Semiconducting Polymer Arrays for Sensitive Photodetectors.

ACS Appl Mater Interfaces 2019 May 22;11(17):15829-15836. Epub 2019 Apr 22.

Key Laboratory of Bio-inspired Materials and Interfacial Science, Technical Institute of Physics and Chemistry , Chinese Academy of Sciences , Beijing 100190 , P. R. China.

Semiconducting conjugated polymers possess attractive optoelectronic properties and low-cost solution processability and are inherently mechanically flexible. However, the device performance is susceptible to the fabrication methods because of the relatively weak intermolecular interaction of the polymers and their inherent conformational and energetic disorder. An efficient fabrication technique for large-scale integration of high-quality polymer architectures is essential for realizing high-performance optoelectronic devices. Here, we report an efficient method for fabrication of polymer nanowire arrays with a precise position, a smooth surface, a homogeneous size, high crystallinity, and ordered molecular packing. The controllable dewetting dynamics on a template with asymmetric wettability permits the formation of discrete capillary bridges, resulting in the ordered molecular packing arising from unidirectional recession of the three-phase contact line. The high quality of nanowire architectures is evidenced by the morphological characteristics and hybrid edge-on and face-on molecular packing with high crystallinity. On the basis of these high-quality nanowire arrays, photodetectors with a responsivity of 84.7 A W and detectivity of >10 Jones are realized. Our results provide a platform for integration of high-quality polymer architectures for use in high-performance optoelectronic devices.
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http://dx.doi.org/10.1021/acsami.8b22562DOI Listing
May 2019

A cyanide-sensing detector in aqueous solution based on anion-π interaction-driven electron transfer.

Analyst 2019 Mar;144(7):2226-2230

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, 2699 Qianjin Avenue, Changchun 130012, P. R. China.

A "turn on" fluorescent and colorimetric sensor, HAT(CN)6, was developed for the light-up detection of cyanide. It was implemented through its strong anion-π interaction, inducing thermal CN- → HAT(CN)6 electron transfer, to give the dianion product [HAT(CN)6]2-, which exhibits unexpected fluorescence. The sensor shows high selectivity, rapid response and a low detection limit towards CN- in aqueous solution, hence indicating its enormous potential in practical applications.
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http://dx.doi.org/10.1039/c9an00135bDOI Listing
March 2019

Multi-stimuli responsive supramolecular gels based on a D-π-A structural cyanostilbene derivative with aggregation induced emission properties.

Soft Matter 2019 Feb;15(7):1658-1665

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, 2699 Qianjin Avenue, Changchun 130012, P. R. China.

Developing multi-stimuli responsive fluorescent gel materials in a single system remains challenging. Gelator molecules with classical fluorophores suffer from the aggregation-caused quenching (ACQ) effect, limiting their applications further. Herein, a novel V-shaped cyanostilbene-based molecule (BAPBIA) with aggregation induced emission (AIE) characteristics and great gelation ability was synthesized and was found to exhibit multi-stimuli responsive behaviors. Reversible gel-sol phase transitions together with emission quenching are realized in response to external stimuli including heat, light and fluoride ions. Especially, the introduction of a dimethylaniline group (donor) and a cyano group (acceptor) generates a D-π-A structure, further leading to an intramolecular charge transfer (ICT) effect, which enlarges the emission contrast with the variation of the distribution of charge. Thus, upon trifluoroacetic acid (TFA) triggered protonation of the dimethylaniline group, not only a gel-sol transition but also emission color switching (yellow-to-blue) is achieved due to the loss of the ICT effect. This work paves an easy way to construct fully reversible multi-stimuli responsive fluorescence modulation smart materials.
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http://dx.doi.org/10.1039/c8sm02434kDOI Listing
February 2019

Fluorescence Regulation and Photoresponsivity in AIEE Supramolecular Gels Based on a Cyanostilbene Modified Benzene-1,3,5-Tricarboxamide Derivative.

Chemistry 2019 Jan 4;25(1):315-322. Epub 2018 Dec 4.

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, 130012, P. R. China.

Supramolecular interactions play an important role in regulating the optical properties of molecular materials. Different arrangements of identical molecules can afford a more straightforward insight into the contributions of supramolecular interactions. Herein, a novel gelator, BTTPA, composed of a benzene-1,3,5-tricarboxamide (BTA) central unit functionalized with three cyanostilbenes is designed, which forms two kinds of gels in DMSO/water mixtures. Depending on the water volume content, the gels exhibit quite different aggregation-induced emission enhancement (AIEE) properties, with one emitting a green emission (G-gel), and the second emitting a blue emission (B-gel). The main reason for this difference is that water affects H-bonding and π-π interactions, further resulting in disparate packing modes of gelators. In addition, only the G-gel displays gel-to-sol transition accompanied with fluorescence switching according to the trans-cis photoisomerization of cyanostilbene under UV light irradiation. The B-gel does not exhibit any change because of its tight hexagonal packing arrangement. Such packing modes restricted the space in which molecules were located and inhibited the transformation of configuration of cyanostilbene. These phenomena underline the incomparable status of packing modes and molecular configuration in regulating fluorescence properties and photoresponse behavior in organic solid-state luminescent materials.
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http://dx.doi.org/10.1002/chem.201804135DOI Listing
January 2019

Fluorescence light-up detection of cyanide in water based on cyclization reaction followed by ESIPT and AIEE.

Analyst 2017 Dec;142(24):4825-4833

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, 2699 Qianjin Avenue, Changchun 130012, P. R. China.

Schiff base 1 (2,4-di-tert-butyl-6-((2-hydroxyphenyl-imino)-methyl)phenol) containing two hydroxyl groups could undergo an oxidative cyclization reaction and then generate hydroxyphenylbenzoxazole (HBO) 2 when CN was present as a catalyst. The multistep cyclization reaction was proved by spectroscopy, H NMR, C NMR and mass spectra. C[double bond, length as m-dash]N isomerization is the predominant decay process of the excited states, so sensor 1 is weakly emissive in solution at ambient temperature. When 1 reacts with CN, the emission is remarkably enhanced, where 1 is converted to 2. The cyclization product HBO 2 displays bright green luminescence in micellar due to the ESIPT (excited-state intramolecular proton transfer) as well as AIEE (aggregation-induced emission enhancement) effect. The detection limit is 5.92 × 10 M, lower than the WHO guideline of CN in drinking water (1.9 μM). The selective and competitive experiments reveal that sensor 1 shows high sensing selectivity and sensitivity for CN over other anions. Test papers containing absorbed 1 were prepared and applied for practical application of cyanide detection.
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http://dx.doi.org/10.1039/c7an01479aDOI Listing
December 2017

Gelation-driven selection in dynamic covalent C 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 C/CN exchange.

Chem Sci 2017 Oct 6;8(10):6822-6828. Epub 2017 Sep 6.

Institut de Science et d'Ingénierie Supramoléculaires (ISIS) , Université de Strasbourg , 8 allée Gaspard Monge , Strasbourg 67000 , France . Email:

Knoevenagel barbiturate derivatives bearing long alkyl chains were proven to form organogels in suitable solvents based on supramolecular interactions. Their reaction with imines allows for component exchange through CC/CN recombination. The effect of various parameters (solvents, chain length, and temperature) on the CC/CN exchange reaction has been studied. Mixing Knoevenagel compound and imine in a 1 : 1 ratio generated a constitutional dynamic library containing the four constituents , , , and . The reversible exchange reaction was monitored by H-NMR, showing marked changes in the fractions of the four constituents on sol-gel interconversion as a function of temperature. The library composition changed from statistical distribution of the four constituents in the sol state to selective amplification of the gel forming constituent together with that of its agonist . The process amounts to self-organization driven component selection in a constitutional dynamic organogel system undergoing gelation. This process displays up-regulation of the gel-forming constituent by component redistribution through reversible covalent connections.
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http://dx.doi.org/10.1039/c7sc02827jDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5643956PMC
October 2017

Single sensor for multiple analytes in different optical channel: Applying for multi-ion response modulation.

Spectrochim Acta A Mol Biomol Spectrosc 2017 Aug 18;183:267-274. Epub 2017 Apr 18.

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, PR China. Electronic address:

A Schiff-base, (2,4-di-tert-butyl-6-((2-hydroxyphenyl-imino)-methyl)phenol) (L), has been improved to function as a simultaneous multi-ion probe in different optical channel. The probe changes from colorless to orangish upon being deprotonated by F, while the presence of Al significantly enhances the fluorescence of the probe due to the inhibition of CN isomerization, cation-induced inhibition of excited-state intramolecular proton transfer (ESIPT), and chelation enhanced fluorescence (CHEF). Dual-channel "off-on" switching behavior resulted from the sequential input of F and Al, reflecting the balance of independent reactions of Al and F with L and with one another. This sensing phenomenon realizes transformation between multiple states and beautifully mimics a "Write-Read-Erase-Read" logic circuit with two feedback loops.
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http://dx.doi.org/10.1016/j.saa.2017.04.026DOI Listing
August 2017

Correction: An efficient phase-selective gelator for aromatic solvents recovery based on a cyanostilbene amide derivative.

Soft Matter 2015 Aug 9;11(30):6162. Epub 2015 Jul 9.

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, 2699 Qianjin Avenue, Changchun 130012, P. R. China.

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http://dx.doi.org/10.1039/c5sm90122gDOI Listing
August 2015

Substituent effects on anion sensing of salicylidene Schiff base derivatives: Tuning sensitivity and selectivity.

Spectrochim Acta A Mol Biomol Spectrosc 2015 Nov 17;150:814-20. Epub 2015 Jun 17.

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, PR China. Electronic address:

A series of colorimetric anion sensors using the salicylidene Schiff bases with different substituents, including electron donating group (tert-butyl, in sensor 2), conjugated group (naphthyl, in sensor 3) and electron withdrawing group (chlorine, in sensor 4), respectively, have been developed. The substituents can not only impact chromogenic signal output, but also tune the sensitivity and selectivity of the anion sensing by their specific electron push-pull features. In particular, both 1 (without substituent) and 2 show high selectivity for F(-) over Cl(-), Br(-), I(-), AcO(-) and H2PO4(-), but the sensitivity of 2 is poorer than 1 due to the effect of electron donating groups. Sensor 3 exhibits higher sensitivity for F(-) than 1, but it is disturbed by the weak response to AcO(-) and H2PO4(-). Sensor 4 has the highest sensitivity for F(-), but shows the significant response to AcO(-) and H2PO4(-), which also decreases the selectivity for F(-). Finally, analytical applications of 1 for the detection of F(-) in aqueous medium and toothpaste have been studied.
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http://dx.doi.org/10.1016/j.saa.2015.06.028DOI Listing
November 2015

A novel cascade strategy with supramolecular and chemodosimetric methods for designing a fluorescent ratiometric detector hypersensitive to trace water.

Analyst 2015 Aug;140(16):5454-8

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun, 130012, P. R. China.

An intensely fluorescent zinc-salicylideneimine complex (-Zn(II)) was developed as a fluorescent ratiometric detector for the quantitative determination of trace water contents both in THF and methanol. It works based on a water-triggered cascade process: the dissociation reaction of the supramolecular ensemble and the subsequent hydrolysis reaction of its ligand.
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http://dx.doi.org/10.1039/c5an00917kDOI Listing
August 2015

An efficient phase-selective gelator for aromatic solvents recovery based on a cyanostilbene amide derivative.

Soft Matter 2015 Jul;11(25):5095-100

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, 2699 Qianjin Avenue, Changchun 130012, P. R. China.

Two novel low molecular weight organogelators (LMOGs) 1 and 2 composed of a cholesteryl group, an amide group and various terminal cyanostilbene moieties were synthesized. They could form stable gels in p-xylene. In particular, 2 with more extended π-conjugation length showed remarkable gelation ability in many aromatic solvents, chloroform and chloroform-containing mixed solvents at a relatively low concentration. FT-IR and XRD spectra indicated that the difference between 1 and 2 in the gelation properties may result from the deviation of the intermolecular hydrogen bonding and π–π stacking as driving forces for the formation of the gels. Significantly, 2 can function as an efficient room-temperature phase-selective gelator (PSG) for potential application in the separation and recovery of various aromatic solvents from its mixture with water. Meanwhile, the gelator can be easily recovered and reused several times. Furthermore, the phase-selective gelation properties of 2 can provide a simple and feasible approach for the removal of the rhodamine B (RhB) dye from water.
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http://dx.doi.org/10.1039/c5sm00898kDOI Listing
July 2015

A highly selective fluorescent sensor for Al³⁺ and the use of the resulting complex as a secondary sensor for PPi in aqueous media: its applicability in live cell imaging.

Dalton Trans 2015 Jul;44(25):11352-9

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, P. R. China.

An easy-to-make salicylimine (L) bearing an "O-N-O"-coordination site was used as a highly selective fluorescent sensor for Al(3+) and PPi in aqueous solution. Sensor L showed a significant fluorescence enhancement in the presence of Al(3+) over other competitive metal ions. It works based on the Al(3+)-induced formation of a 1 : 1 L-Al(3+) complex, producing a chelation-enhanced fluorescence effect, the fluorescence quantum yield reached 0.59. This L-Al(3+) ensemble is a subsequent fluorescent sensor for PPi due to the strong attraction between Al(3+) and PPi, it can selectively discriminate PPi overcoming the interference of the biological competitors including PO4(3-), ADP and ATP at physiological pH. L and L-Al(3+) exhibit high sensitivity and selectivity for Al(3+) and PPi, the detection limits were found to be as low as 2.94 × 10(-8) M and 2.74 × 10(-7) M, respectively. It was further confirmed that sensor L had potential practical applications through mapping of Al(3+) in live cells.
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http://dx.doi.org/10.1039/c5dt00689aDOI Listing
July 2015

A real-time fluorescent sensor specific to Mg2+: crystallographic evidence, DFT calculation and its use for quantitative determination of magnesium in drinking water.

Dalton Trans 2015 Feb;44(6):2755-62

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun, 130012, P. R. China.

An "off-the-shelf" fluorescence "turn-on" Mg(2+) chemosensor 3,5-dichlorosalicylaldehyde (BCSA) was rationally designed and developed. This proposed sensor works based on Mg(2+)-induced formation of the 2 : 1 BCSA-Mg(2+) complex. The coordination of BSCA to Mg(2+) increases its structural rigidity generating a chelation-enhanced fluorescence (CHEF) effect which was confirmed by single crystal XRD studies of the BSCA-Mg(2+) complex and TD/DFT calculations. This sensor exhibits high sensitivity and selectivity for the quantitative monitoring of Mg(2+) with a wide detection range (0-40 μM), a low detection limit (2.89 × 10(-7) mol L(-1)) and a short response time (<0.5 s). It can also resist the interference from the other co-existing metal ions, especially Ca(2+). Consequently, this fluorescent sensor can be utilized to monitor Mg(2+) in real time within actual samples from drinking water.
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http://dx.doi.org/10.1039/c4dt03068kDOI Listing
February 2015

Adaptation in constitutional dynamic libraries and networks, switching between orthogonal metalloselection and photoselection processes.

J Am Chem Soc 2014 Jul 17;136(26):9509-18. Epub 2014 Jun 17.

Laboratoire de Chimie Supramoléculaire, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Université de Strasbourg , 8 Allée Gaspard Monge, 67000 Strasbourg, France.

Constitutional dynamic libraries of hydrazones (a)A(b)B and acylhydrazones (a)A(c)C undergo reorganization and adaptation in response to a chemical effector (metal cations) or a physical stimulus (light). The set of hydrazones [(1)A(1)B, (1)A(2)B, (2)A(1)B, (2)A(2)B] undergoes metalloselection on addition of zinc cations which drive the amplification of Zn((1)A(2)B)2 by selection of the fittest component (1)A(2)B. The set of acylhydrazones [E-(1)A(1)C, (1)A(2)C, (2)A(1)C, (2)A(2)C] undergoes photoselection by irradiation of the system, which causes photoisomerization of E-(1)A(1)C into Z-(1)A(1)C with amplification of the latter. The set of acyl hydrazones [E-(1)A(1)C, (1)A(3)C, (2)A(1)C, (2)A(3)C] undergoes a dual adaptation via component exchange and selection in response to two orthogonal external agents: a chemical effector, metal cations, and a physical stimulus, light irradiation. Metalloselection takes place on addition of zinc cations which drive the amplification of Zn((1)A(3)C)2 by selection of the fittest constituent (1)A(3)C. Photoselection is obtained on irradiation of the acylhydrazones that leads to photoisomerization from E-(1)A(1)C to Z-(1)A(1)C configuration with amplification of the latter. These changes may be represented by square constitutional dynamic networks that display up-regulation of the pairs of agonists ((1)A(2)B, (2)A(1)B), (Z-(1)A(1)C, (2)A(2)C), ((1)A(3)C, (2)A(1)C), (Z-(1)A(1)C, (2)A(3)C) and the simultaneous down-regulation of the pairs of antagonists ((1)A(1)B, (2)A(2)B), ((1)A(2)C, (2)A(1)C), (E-(1)A(1)C, (2)A(3)C), ((1)A(3)C, (2)A(1)C). The orthogonal dual adaptation undergone by the set of acylhydrazones amounts to a network switching process.
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http://dx.doi.org/10.1021/ja504813rDOI Listing
July 2014

A dual channel optical detector for trace water chemodosimetry and imaging of live cells.

Analyst 2013 May;138(10):2847-57

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun, 130012, P. R. China.

A novel 3-5-dichlorosalicylaldehyde Schiff base chemodosimeter (compound 1) for water is designed and synthesized, and it works based on a water-triggered reaction of a Schiff base. Addition of trace amounts of water into 1 in various organic solvents leads to a fluorescence turn-on response and a simultaneous dual-channel signal modulation (both in the fluorescence and absorption spectra). Especially, 1 is found to be an outstanding fluorescence enhancement water sensor in methanol with an extremely low detection limit of 22 ppm. Consequently this probe can be utilized to detect trace water in commercial methanol. The quantitative detection of a wide range of water content is enhanced in THF and acetonitrile (0-35% v/v for THF and 0-20% v/v for acetonitrile), where the fluorescence peak intensity is nearly proportional to the amount of water added. Moreover, 1 can be used for monitoring pH through a novel ON-OFF-ON type signal modulation both in fluorescence and absorption spectra within a wide pH detection range. Thus, the chemodosimeter can not only be utilized to monitor the intracellular pH fluctuations, but also to accomplish simultaneous in situ staining of the cytosol and acidic organelles in two different channels, respectively.
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http://dx.doi.org/10.1039/c3an36887dDOI Listing
May 2013

Fluoride-responsive gelator and colorimetric sensor based on simple and easy-to-prepare cyano-substituted amide.

Org Biomol Chem 2012 Sep 30;10(34):6973-9. Epub 2012 Jul 30.

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, P.R. China.

A new and easy-to-prepare gelator based on cyano-substituted amide (BPNIA) was designed and synthesized. BPNIA could form thermoreversible gel in DMSO-H(2)O (v/v, 9 : 1) and ultrasound-stimulated gel in DMSO. FT-IR, UV-vis and XRD spectra indicated that the gelator molecules self-assemble into a fibrous network resulting from the cooperation of intermolecular hydrogen bonding, π-π stacking and cyano interactions. BPNIA can act as a highly selective colorimetric sensor for fluoride in DMSO, overcoming the interference of H(2)PO(4)(-), AcO(-) and other halide anions. The deprotonation of the NH groups is responsible for the dramatic color change from colorless to yellow. Interestingly, the organogel of BPNIA could allow a two channel fluoride response by proton controlled reversible sol-gel transition and color changes.
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http://dx.doi.org/10.1039/c2ob26016fDOI Listing
September 2012

Uniformly gold nanoparticles derived from P2VP-b-PCHMA block copolymer templates with different reduction methods.

J Nanosci Nanotechnol 2011 Aug;11(8):6973-8

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, P. R. China.

The micellization of poly(2-vinylpyridine)-block-poly(cyclohexyl methacrylate) (P2VP-b-PCHMA) in THF can be induced by the complexation between the P2VP blocks and HAuCl4, forming composite polymeric micelles with PCHMA being the shell and P2VP/HAuCl4 complex being the core. In order to obtain regular arrays of gold nanoparticles (Au NPs), monolayer of HAuCl4-loaded surface micelles have been produced by spin-coating the micellar solution, and Au NPs in different size have been obtained by oxygen plasma with different reduction processes. In addition, pyrole (PY) has been used as an efficient reducing agent to fabricate dispersed Au NPs within micellar structure in a short reducing time, resulting in a raspberry-like morphology of the Au-polymer composites. With the addition of annealing processes or longer reducing time (one month), different shapes of Au NPs have been observed in the cast films. Furthermore, core-shell nanostructures of gold-polypyrole (Au-PPY) have also been observed by employing vapor phase polymerization of PY onto HAuCl4-loaded polymeric solution-cast films.
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http://dx.doi.org/10.1166/jnn.2011.4211DOI Listing
August 2011

Micropatterning of Ag and Au nanoparticles by microcontact printing and block copolymer micelles.

J Nanosci Nanotechnol 2011 Feb;11(2):1135-40

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, PR China.

Micropatterns of gold and silver nanoparticles were successfully obtained by combining microcontact printing and poly(2-vinylpyridine)-block-poly(cyclohexyl metharylate) (P2VP-b-PCHMA) diblock copolymer micelles with metal precursors. The metal ions were incorporated into poly(2-vinylpyridine) blocks and located into the core area of micelles. Then the metal-loaded micellar solutions were used as inks which were spin coated as thin layers onto polydimethylsiloxane stamps and transferred onto the substrates by stamping. Different morphologies of micellar aggregates were formed on the substrates depending on the stamp morphologies, and single layers of nanoparticles in the micropattern were obtained by the reducing process.
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http://dx.doi.org/10.1166/jnn.2011.3077DOI Listing
February 2011

A molecular half-subtractor with Zn2+ and UV-light as inputs.

Spectrochim Acta A Mol Biomol Spectrosc 2010 Sep 24;77(1):226-31. Epub 2010 May 24.

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, PR China.

The salen-type Schiff base (2,2'-bis(2-hydroxybenzylideneamino)-1,1'-binaphthyl (BHB)) has been synthesized and characterized. Exhibiting absorption and fluorescence changes in the presence of Zn(2+) in chloroform and ethanol mixed solution, BHB could be used as a fluorescent chemosensor for the detection of Zn(2+). Furthermore, by monitoring the fluorescence and absorbance as output signals, BHB can function as a combinatorial logic circuit for a molecular half-subtractor with Zn(2+) and UV irradiation as input variables.
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http://dx.doi.org/10.1016/j.saa.2010.05.013DOI Listing
September 2010

Patterned carbon nanotubes fabricated by the combination of microcontact printing and diblock copolymer micelles.

J Nanosci Nanotechnol 2010 Jan;10(1):508-13

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, PR China.

A convenient approach to synthesize patterned carbon nanotubes (CNTs) of three morphologies on printed substrates by combination of microcontact printing (microCP) and a plasma-enhanced chemical vapor deposition (PECVD) process is presented. Micelles of polystyrene-block-poly-(2-vinylpyridine) (PS-b-P2VP) in toluene were used as nanoreactors to fabricate FeCl3 in the core domains, and the complex solution was used as an ink to print films with polydimethylsiloxane (PDMS) stamps, different morphologies (porous, dots and stripes patterns) of the FeCl3-loaded micellar films were left onto silicon substrates after printed. After removing the polymer by thermal decomposition, the left iron oxide cluster arrays on the substrate were used as catalysts for the growth of CNTs by the process of PECVD, where the CNTs uniformly distributed on the substrates according to the morphologies of patterned catalysts arrays.
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http://dx.doi.org/10.1166/jnn.2010.1587DOI Listing
January 2010

Hydrogen-bonding A(LS)2-type low-molecular-mass gelator and its thermotropic mesomorphic behavior.

J Colloid Interface Sci 2009 Oct 21;338(2):463-7. Epub 2009 Jun 21.

State Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699 Qianjin Avenue, Changchun 130012, PR China.

A unique cholesterol-based A(LS)2-type gelator, which is a hydrogen-bonding complex based on an ALS-type non-gelator molecule 3-cholesteryl 4-(trans-2-(4-pyridinyl)vinyl)phenyl succinate and a counterpart 3-cholesteryloxycarbonylpropanoic acid, shows strong gelation ability in alcohol and aromatic solvents. The formed gel has a high Tg at low gelation concentration, and its xerogel shows fibrillar microstructure revealed by scanning electron microscopy (SEM). FTIR confirms the existence of intermolecular hydrogen bond in the gelator, and X-ray diffraction (XRD) analysis reveals that the gelator possesses a folded conformation in gel and self-assembles into the fibrillar structure mainly by van der Waals interaction between cholesteryl moieties of the gelator. Further more, the thermotropic behavior of the xerogel is studied by differential scanning calorimetry (DSC) and polarized optical microscopy (POM), which shows typical optical textures of liquid crystals.
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http://dx.doi.org/10.1016/j.jcis.2009.06.034DOI Listing
October 2009

Alkyl and dendron substituted quinacridones: synthesis, structures, and luminescent properties.

J Phys Chem B 2007 May 18;111(19):5082-9. Epub 2007 Apr 18.

Key Laboratory for Supramolecular Structure and Materials of Ministry of Education, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China.

The synthesis of two alkyl substituted quinacridone derivatives, N,N'-di(n-hexyl)-1,3,8,10-tetramethylquinacridone (1) and N,N'-di(n-hexyl)-2,9-di(t-butyl)quinacridone (2), and four dendritic quinacridone derivatives, N,N'-didendritic-1,3,8,10-tetramethylquinacridones (3-G1 and 3-G2) and N,N'-didendritic-2,9-di(tert-butyl)quinacridones (4-G1 and 4-G2) are reported. X-ray crystal structure and thermal analysis revealed that the quinacridone derivatives reported in this paper exhibit the evolution from crystalline phase to amorphous phase upon varying from alkyl substituted quinacridones to dendritic quinacridones. The concentration-dependent 1H NMR, UV-vis, and photoluminescence (PL) spectroscopic studies demonstrated the aggregation properties of the quinacridone derivatives in solution. For dendritic quinacridones with the sufficient shield of dendrons, the fluorescence concentration quenching can be significantly suppressed and emission intensity in concentrated solution and solid state could be greatly enhanced. Compound 4-G2 displays good solution process property and higher PL yield in concentrated solution, suggesting that it is a potential candidate for the fabrication of high-performance organic electroluminescent devices (OLEDs) on the basis of low-cost solution process technique.
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http://dx.doi.org/10.1021/jp068646mDOI Listing
May 2007
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