Polymorphic crystals and their luminescence switching of triphenylacrylonitrile derivatives upon solvent vapour, mechanical, and thermal stimuli

Zhang, Yujian; Song, Qingbao; Wang, Kai; Mao, Wengang; Cao, Feng; Sun, Jingwei; Zhan, Lingling; Lv, Yaokang; Ma, Yuguang; Zou, Bo; Zhang, Cheng

doi:10.1039/c4tc02826k

Cited by 83 publications

(38 citation statements)

References 50 publications

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“…1b). [63][64][65][66] This was further supported by HOMO-LUMO calculation. It has been reported in the literature that nanofabrication of organic functional materials often lead to tunable fluorescence by change of nanoparticles size, shape and 55 phase.…”

Section: Structural Analysismentioning

confidence: 66%

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Reversible fluorescence switching and topochemical conversion in an organic AEE material: polymorphism, defection and nanofabrication mediated fluorescence tuning

Hariharan

Moon²,

Anthony

2015

J. Mater. Chem. C

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2-(4-(diphenylamino)-2-methoxybenzylidene) malononitrile (DPAMBM), an organic aggregation enhanced emission material, showed external stimuli mediated reversible phase change (crystalline to amorphous) and fluorescence switching as well as multiple factor mediated fluorescence tuning in the solid state. Polymorphic crystals obtained from CH 3 CN (DPAMBM-1) and CH 3 OH ( DPAMBM-2) 10 exhibited fluorescence at 588 nm and 538 nm, respectively. Single crystal analysis showed slightly twisted molecular conformation between aminophenyl (donor) and malononitrile (acceptor) and the molecules are well separated in the crystal lattice. Whereas linear molecular conformation and strong intermolecular interaction with anti-parallel dipole arrangement was observed in DPAMBM-2. Slight breaking and strong grinding of DPAMBM-1 crystals showed blue shifting of fluorescence to 571 nm and 15 562 nm, respectively. Interestingly, annealing/solvent vapor exposure further blue shift the fluorescence to 545 nm and convert the grounded powder to DPAMBM-2. Strong grinding of DPAMBM-2 red shifted the fluorescence to 562 nm and annealing/vapor exposure switched back to 545 nm. DPAMBM-2 was converted to DPAMBM-1 by annealing at 120 °C that tuned the fluorescence from 538 nm to 572 nm and mechanical grinding and annealing further blue shift the fluorescence to 545 nm. Nanofabrication of 20 DPAMBM also showed fluorescence tuning from 562 nm to 536 nm due to morphological change. Thus DPAMBM showed a rare combination of gradual fluorescence tuning from 588 nm to 536 nm and external stimuli controlled phase change with fluorescence switching between 545 nm and 562 nm.

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Section: Structural Analysismentioning

confidence: 66%

“…It has been reported in the literature that nanofabrication of organic functional materials often lead to tunable fluorescence by change of nanoparticles size, shape and 55 phase. 64,66 Quantum yield measurement of solids 50 showed higher fluorescence intensity for DPAMBM-2 compared to DPAMBM-1. 1c, S2 (a,b), S4).…”

Section: Structural Analysismentioning

confidence: 98%

Reversible fluorescence switching and topochemical conversion in an organic AEE material: polymorphism, defection and nanofabrication mediated fluorescence tuning

Hariharan

Moon²,

Anthony

2015

J. Mater. Chem. C

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“…Moreover, these void‐like structures are deformable and tend to give easy distortion, which makes them interesting candidates for stimuli‐responsive materials. In fact, TPAN molecules can exhibit rich behavior such as polymorphism and multistimuli fluorescence switching by thermal, mechanical, or vapor stimuli . A modular analysis proved useful to analyze and interpret the complex structure/luminescence relationship in highly twisted TPAN conjugated molecules in which polymorphism is due to slight differences in molecular torsional angles and sparse π‐stackings .…”

Section: Solid‐state: Polycrystalline Powders Single Crystals and Tmentioning

confidence: 99%

Self‐Assembled α‐Cyanostilbenes for Advanced Functional Materials

2017

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In the specific context of condensed media, the significant and increasing recent interest in the α-cyanostilbene (CS) motif [ArCHC(CN)Ar] is relevant. These compounds have shown remarkable optical features in addition to interesting electrical properties, and hence they are recognized as very suitable and versatile options for the development of functional materials. This progress report is focused on current and future use of CS structures and molecular assemblies with the aim of exploring and developing for the next generations of functional materials. A critical selection of illustrative materials that contain the CS motif, including relevant subfamilies such as the dicyanodistyrylbenzene and 2,3,3-triphenylacrylonitrile shows how, driven by the self-assembly of CS blocks, a variety of properties, effects, and possibilities for practical applications can be offered to the scientific community, through different rational routes for the elaboration of advanced materials. A survey is provided on the research efforts directed toward promoting the self-assembly of the solid state (polycrystalline solids, thin films, and single crystals), liquid crystals, nanostructures, and gels with multistimuli responsiveness, and applications for sensors, organic light-emitting diodes, organic field effect transistors, organic lasers, solar cells, or bioimaging purposes.

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“…The development of photoactive materials is an actively researched field that is accelerating innovations and, consequently, improving human condition . These materials are used in many high‐tech applications, including optoelectronic systems, stimuli‐responsive materials, and sensors . As a result, new approaches and phenomena are pursued with the aim of developing the next‐generation photoactive materials.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Synthesis of Dual‐Emissive Tetraphenylethene‐Based Dendrimers with Tunable Aggregates and Solution States Emissions

Abd‐El‐Aziz

Agatemor

Etkin

et al. 2016

Macromol. Rapid Commun.

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Photoactive materials are actively researched, piloting breakthroughs that have enriched fundamental understanding of science, and have led to real applications. Tetraphenylethene, a photoactive molecule that is of interest from fundamental and applied perspectives, features photochemical properties that are not exploited in the design of photoactive, dual-emissive materials. Here, tetraphenylethene-based, dual-emissive dendrimers are constructed via a synthetic approach that involves a photochemical reaction that exploits the photochemistry of tetraphenylethene. These dendrimers are emissive in solution and in the aggregate state with tunable dual emissions at 368 and 469 nm. The photochemical reaction also tunes the size of the aggregates, increasing the size after UV irradiation. The reported synthetic strategy is a direct and facile approach to accessing dual-emissive macromolecules, especially tetraphenylethene-based systems for real applications.

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Polymorphic crystals and their luminescence switching of triphenylacrylonitrile derivatives upon solvent vapour, mechanical, and thermal stimuli

Cited by 83 publications

References 50 publications

Reversible fluorescence switching and topochemical conversion in an organic AEE material: polymorphism, defection and nanofabrication mediated fluorescence tuning

Reversible fluorescence switching and topochemical conversion in an organic AEE material: polymorphism, defection and nanofabrication mediated fluorescence tuning

Self‐Assembled α‐Cyanostilbenes for Advanced Functional Materials

Photoinduced Synthesis of Dual‐Emissive Tetraphenylethene‐Based Dendrimers with Tunable Aggregates and Solution States Emissions

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