Locking the phenyl rings of tetraphenylethene step by step: understanding the mechanism of aggregation-induced emission

Shi, Junqing; Chang, Ning Hui; Li, Chun‐Zhu; Mei, Ju; Deng, Chunmei; Luo, Xichun; Liu, Zheng­ping; Bo, Zhishan; Dong, Yong Qiang; Tang, Ben Zhong

doi:10.1039/c2cc35641d

Cited by 233 publications

(147 citation statements)

References 18 publications

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“…This restriction blocks the non-radiative pathway and opens up the radiative channel. 18,19 Besides when in aggregate state, AIEgens can also emit uorescence when they are restricted with the help of surrounding polymer chains by covalent bond. Our group previously reported a facile approach to synthesize stimuliresponsive uorescent elastomer by linking tetraphenylethylene (TPE) derivant to exible polydimethylsiloxane (PDMS) polymer chains with covalent-bond.…”

Section: 10mentioning

confidence: 99%

Studying a novel AIE coating and its handling process via fluorescence spectrum

Yao

Wang

et al. 2017

RSC Adv.

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For polymer materials, both their compositions and preparation process greatly influence their service performance. Thus, the sound understanding of the relationship between materials' preparation processes and their properties is paramount. However, current research methods are partially limited due to the absence of a direct testing method to track the entire process, e.g. synthesizing, curing, ageing, and so on. With the ability for real-time sensitive characterization, fluorescence spectroscopy may be applied in testing polymer materials' performance. Here, we synthesized a novel aggregation induced emission (AIE) resin named TPE-EPOXY resin and prepared an AIE coating based on it.According to restriction of intramolecular rotation (RIR) mechanism, the preparation, curing, and aging processes for the AIE polymer resins & coatings could be studied with real-time observation. In addition, their properties could also be studied systematically. The results in this paper pave a good way to understand the relationship between the internal structure and the properties of polymer materials.Moreover, the prepared AIE polymer resins has a potential to expand the application fields of the AIE mechanism.

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Section: 10mentioning

confidence: 99%

Studying a novel AIE coating and its handling process via fluorescence spectrum

Yao

Wang

et al. 2017

RSC Adv.

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“…The twisted, propeller-shaped 9 was described as an ethene stator completely surrounded by phenyl rotors [23]. Very recently, it was discovered that locking the phenyl rings in 9 with ''O'' bridges to give diphenylmethylenexanthene (8) and dixanthylene (2) increases gradually the emission efficiency of luminogen solutions, thus supporting the restriction of intermolecular rotation (RIR) mechanism of the AIE phenomenon [22,26]. By contrast, introducing naphthalenyl substituents at the x positions of the 9-methylene-tricyclic aromatic enes in place of the respective benzene rings to give e.g., 10 may enhance the overcrowding [24,25].…”

Section: Introductionmentioning

confidence: 99%

“…The following two variations leading to open BAEs exist: (i) removal of one bridge (X or Y) of the BAE to give BAE-1, i.e., mono-bridged tetraarylethene e.g., 9-diphenylmethylen-9H-fluorene (7) [21] and-9-diphenylmethylen-9H-xanthene (8) [22]; and (ii) removal of the two bridges of BAE to give BAE-2, i.e., tetraarylethene, e.g., tetraphenylethene (9) [23] and tetrakis (2-naphthalenyl)ethene (10) [24,25]. Removal of the ring constraint (and of p-delocalization when the central ring had aromatic character) facilitates rotations of the aryl groups about the formal single C-C bonds between the ene carbon atoms (C 9 and/or C 9 0 ) and the aryl group bonded to C 9 and/or C 9 0 .…”

Section: Introductionmentioning

confidence: 99%

“…The following BAE-1s with 1-naphthalenyl and 2-naphthalenyl substituents at the x position of the 9-methylene-fluorenylidene and chalcogenoxanthene were targeted: (Fig. 2): 9-(di-1-naphthalenylmethylene)-9H-fluorene (11), 9-(di-1-naphthalenylmethylene)-9H-xanthene (12), 9-(di-1-naphthalenylmethylene)-9H-thioxanthene (13), 9-(di-1-naphthalenyl methylene)-9H-selenoxanthene (14), 9-(di-1-naphthalenylmethylene)-9H-telluroxanthene (15), 9-(di-2-naphthalenylmethylene)-9H-fluorene (16), 9-(di-2-naphthalenylme thylene)-9H-xanthene (17), 9-(di-2-naphthalenylmethylene)-9H-thioxanthene (18), 9-(di-2-naphthalenylmethylene)-9H-selenoxanthene (19), 9-(di-2-naphthalenylmethyl ene)-9H-telluroxanthene (20), 9-(di-1,2 0 -naphthalenylmethylene)-9H-fluorene (21), 9-(di-1,2 0 -naphthalenylmethylene)-9H-xanthene (22), 9-(di-1,2 0 -naphthalenylmethyle ne)-)-9H-thioxanthene (23), 9-(di-1,2 0 -naphthalenylmethyl ene)-9H-selenoxanthene (24), and 9-(di-1,2 0 -naphthalenylmethylene)-9H-telluroxanthene (25).…”

Section: Introductionmentioning

confidence: 99%

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Variations of bistricyclic aromatic enes: mono-bridged tetraarylethene naphthologs

et al. 2014

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The syntheses, molecular and crystal structures, NMR spectroscopic study, and DFT computational study of naphthologs of mono-bridged (X = -, O, S, Se, and Te) tetraarylethene (BAE-1s) 11-25 with a,a-, b,b-, and a,b-dinaphthalenyl substituents have been reported. The BAE-1s have been prepared by Barton-Kellog twofold extrusion from the respective chalcogenothiones and diazomethylenebisnaphthylenes. Complete assignments of 1 Hand 13 C-NMR spectra of 11-25 have been made through 2-dimensional correlation spectroscopy (DQF-COSY, HSQC, HMBC, and NOESY). The corresponding intermediates, thiiranes 33-47, have been also isolated (except 38), and their molecular and crystal structures have been determined. The molecular structures of BAE-1s 12-15, 20, and 22-25 adopted folded-twisted conformations with considerably folded (u = 30°-57°) tricyclic moieties. The a,a-and a,b-dinaphthalenyl derivatives are more overcrowded than b,b-dinaphthalenyl derivatives. The relief of the steric strain due to the overcrowding around C 9 = C 9 0 caused by the presence of naphthalenyl substituents was achieved by their twisting around the single bonds that connect the a-naphthalenyl and b-naphthalenyl moieties to C 9 0 . The 1 H-NMR spectra have shown shielding of H 2 , H 7 of 11-25 and the pronounced deshielding of H 8 0 , H 8 00 of a,a-dinaphthalenyl-substituted BAE-1s 13-15 in contrast to b,b-dinaphthalenyl-substituted BAE-1s 16-20. The upfield shifts of H 2 , H 7 suggested conformations in which these hydrogens are located above the planes of the opposing naphthalene rings. DFT calculations of 11-20 have been performed at B3LYP/6-31G(d) and B3LYP/ SDD. The results have shown that the global minima of BAE-1s without a chalcogen bridge 11 and 16 are twisted (-sc,-sc)-C 2 -t conformations. The global minima of BAE1s with a chalcogen bridge are folded-twisted (-sc,-ac)-C 1 -ft conformations for a,a-dinaphthalenyl-substituted BAE1s 12-15 and either anti-or syn-(-sc,ac)-C 1 -ft conformations for b,b-dinaphthalenyl-substituted BAE-1s 17-20. The pronounced differences between the a,a-dinaphthalenyl and the b,b-dinaphthalenyl derivatives are noted. Dispersion-corrected B3LYP calculations stabilize significantly the a,a-dinaphthalenyl derivatives versus the b,b-dinaphthalenyl derivatives. The geometrical parameters of BAEs-1 11-15 and 20, derived from their molecular X-ray structures and from their B3LYP-optimized geometries are in a good agreement.

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“…Our unprecedented TR PL hydrogels should be able to enrich the potential applications of the TPE-type molecules, since they function over a broad temperature range. 4,[14][15][16][17][18][19][20][21]24 Furthermore, the present design and synthesis of the d-TPE-doped PS-co-PNIPAM/PNIPAM-co-PAA hydrogel nanoparticles should shed light on a general methodology that leads to functional hydrogels with sensitive responses to external stimuli. 15 Preparation of PS-co-PNIPAM Core Nanoparticles and PS-co-PNIPAM/PNIPAM-co-PAA Core−Shell Nanoparticles.…”

Section: ■ Introductionmentioning

confidence: 99%

Interfacing a Tetraphenylethene Derivative and a Smart Hydrogel for Temperature-Dependent Photoluminescence with Sensitive Thermoresponse

Jiang

Yang

et al. 2014

ACS Appl. Mater. Interfaces

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Locking the phenyl rings of tetraphenylethene step by step: understanding the mechanism of aggregation-induced emission

Cited by 233 publications

References 18 publications

Studying a novel AIE coating and its handling process via fluorescence spectrum

Studying a novel AIE coating and its handling process via fluorescence spectrum

Variations of bistricyclic aromatic enes: mono-bridged tetraarylethene naphthologs

Interfacing a Tetraphenylethene Derivative and a Smart Hydrogel for Temperature-Dependent Photoluminescence with Sensitive Thermoresponse

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