Substitution position tuning of the different aggregation-induced emission properties of four (1-naphthyl)vinyl(9-anthryl)vinylbenzene isomers: from ACQ to AIEE and AIE

Li, Ye-Xin; Pang, Mao-Ping; Zhang, Zhenwei; Li, Guobao; Sun, Guangmin

doi:10.1039/c3ra40612a

Cited by 21 publications

(25 citation statements)

References 17 publications

(4 reference statements)

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“…For QC-F6 with a lower FITC content, the fluorescence intensity increased with concentration, and the maximum emission peak remained the same (Figure b). For QC-F11 with a higher FITC content, the fluorescence intensity increased with concentration from 0.1 to 0.5 mg/mL, above which the fluorescence intensity decreased and the maximum emission peak shifted bathochromically (Figure c), indicating the aggregation of FITC units. The maximum fluorescence intensity versus the concentration of QC-F2, QC-F6, QC-F8, and QC-F11 is shown in Figure d.…”

Section: Resultsmentioning

confidence: 78%

Fluorescent Amphiphilic Quaternized β-Chitin: Antibacterial Mechanism and Cell Imaging

Xie

et al. 2021

ACS Appl. Bio Mater.

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Fluorescent materials span multiple applications from biological probes and chemical sensing to optoelectronic systems. Although great efforts have been made toward developing classes of fluorescent materials, 100,000+ traditional fluorescent dyes still suffer from the obstacle of aggregation-caused quenching (ACQ). Thus, designing fluorescent materials with excellent optical performance from ACQ luminogens remains challenging. In this work, we prepared fluorescent amphiphilic quaternized β-chitin (QC-F) via nucleophilic addition between the amino groups of QC and isothiocyanate groups of fluorescein isothiocyanate (FITC). Due to the covalent anchoring of the QC backbone, steric hindrance of the bulky acetamido groups, electrostatic repulsion of the quaternary ammonium groups, and homogeneous distribution of FITC units, the FITC units were spatially and electronically isolated, and the QC-F series exhibited unique fluorescent behaviors. The QC-F series could be used to observe their interactions with microbial cells through fluorescence imaging to gain insights into the QC antibacterial mechanism. Moreover, with their favorable cytocompatibility, the QC-F series are also suitable for cell imaging. Thus, the present work will broaden the applications of chitin and conventional ACQ luminogens.

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Section: Resultsmentioning

confidence: 78%

Fluorescent Amphiphilic Quaternized β-Chitin: Antibacterial Mechanism and Cell Imaging

Xie

et al. 2021

ACS Appl. Bio Mater.

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“…All of these π-conjugates are soluble in most of the water-miscible solvents and significantly stable under photoexcitation in both the solution and solid states, whereas the photostability was an issue for the previously reported system with similar properties, in which two 9-vinylanthracene parts are attached to only 1,2-positions of the benzene ring. 10…”

Section: Results and Discussionmentioning

confidence: 99%

“…With this clue, we were earlier successful to generate distinct anthracenyl π-conjugates 9 as new AIEgens, including these two pyridyl analogues ATh4P and AT4P (9b) (Figure 2), where AT4P was established as multiple metal-ion sensors. 9c Meanwhile, the literature reports on the substitution 10 and regioisomeric effect 11 on the AIE behavior due to different molecular packing in the aggregate state and electronic structure prompted us to synthesize a variety of regioisomeric pyridyl compounds (Figure 2) and explore their photophysical behaviors in both solution and aggregate states.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, such molecules with the same molecular formulae can display different photophysical behavior just because of the different conformational flexibility within the molecule. 10 At present, we focus on generating and studying the AIE properties for three series of regioisomeric pyridyl π-conjugates that are linked with (hetero)aryl-substituted anthracene (Figure 2). The subtle change in the position of nitrogen for the pyridyl ring resulted in different absorption and emission behaviors on aggregation.…”

Section: Introductionmentioning

confidence: 99%

“…More importantly, a precise change in the position of pyridyl nitrogen atom by keeping the other part intact was expected to exert a substantial effect on the molecular conformation, crystal packing, electronic structure, and subsequently the optical properties. Thus, such molecules with the same molecular formulae can display different photophysical behavior just because of the different conformational flexibility within the molecule . At present, we focus on generating and studying the AIE properties for three series of regioisomeric pyridyl π-conjugates that are linked with (hetero)aryl-substituted anthracene (Figure ).…”

Section: Introductionmentioning

confidence: 99%

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Positional Variation of Monopyridyl-N in Unsymmetrical Anthracenyl π-Conjugates: Difference between Solution- and Aggregate-State Emission Behavior

et al. 2019

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Fluorescence enhancement on aggregation for π-conjugates linked with pyridyl ring has been established as a part of widely studied smart organic functional materials. Therefore, the photophysical features in the solution and aggregate states for such compounds remain impressive. In this work, we synthesized three series of photostable unsymmetrical aryl-substituted anthracenyl π-conjugates linked to pyridyl ring with a variation of the position of a pyridyl-N atom and examined the difference in the photophysical properties preferably in the aggregate state. The so-called “aggregation-induced emission (AIE)” behavior was discernible for the 2- and 4-pyridyl- but not 3-pyridyl-10- p -tolyl or mesityl-substituted π-conjugates. Curiously, a variation of the position of a pyridyl-N atom does not solely control the AIE phenomenon for 10-thiophenyl-substituted π-conjugates, where all of the isomers are found to be AIE-active. Hence, the dissimilarity in emission behavior in the aggregate state is governed by the position of N-atom for pyridine and also the substituent at the 10th position of the anthracyl ring. The mechanistic insight behind these observations is demonstrated by concentration-dependent fluorescence studies, time-resolved fluorescence, single-crystal X-ray diffraction studies (largely supportive to understand the molecular structure and packing in the aggregate), and average particle size measurement of the aggregates and partly by the density functional theory studies for a few representative molecules.

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Cellulose‐Based Solid Fluorescent Materials

Tian

Zhang

et al. 2016

Advanced Optical Materials

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Organic solid‐state fluorescent materials have exhibited great potential application in optoelectronics, imaging, sensing, and security printing. However, the conventional conjugated luminogens such as perylene and pyrene derivatives are not highly recommended for preparation of the solid fluorescent materials because they always undergo fluorescence self‐quenching in solid state, i.e., aggregation caused quenching (ACQ) phenomenon. Herein, a series of solid materials with excellent fluorescent emission have been realized via covalently bonding the ACQ luminogens onto the cellulose chains and subsequently ionizing process. The synergy between the anchoring and diluting effect on luminogens of cellulose skeleton and the electrostatic repulsion among the ACQ luminogens efficiently inhibits the aggregation and the self‐quenching of luminogens. Such a general strategy is suitable for different ACQ luminogens and various partially substituted cellulose derivatives. Furthermore, the prepared fluorescent solids preserve the excellent properties of original cellulose derivatives such as good solubility and processibility. Therefore, they can be readily processed into materials in different forms, including printing pattern, coating, film, fiber, colloid, etc. This simple and effective strategy gives added impetus to the applications of solid fluorescent materials in practice.

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Substitution position tuning of the different aggregation-induced emission properties of four (1-naphthyl)vinyl(9-anthryl)vinylbenzene isomers: from ACQ to AIEE and AIE

Abstract: The variation in the substitution position exerts a much more distinct influence on the solution optical properties of four NAB isomers, which leads to totally different emission behaviors.ESI 3 ). 1,2-NAB was prepared using the same procedure described for 1,3-NAB.

Cited by 21 publications

References 17 publications

Fluorescent Amphiphilic Quaternized β-Chitin: Antibacterial Mechanism and Cell Imaging

Fluorescent Amphiphilic Quaternized β-Chitin: Antibacterial Mechanism and Cell Imaging

Positional Variation of Monopyridyl-N in Unsymmetrical Anthracenyl π-Conjugates: Difference between Solution- and Aggregate-State Emission Behavior

Cellulose‐Based Solid Fluorescent Materials

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