Effect of ionic interaction on the mechanochromic properties of pyridinium modified tetraphenylethene

Hu, Ting; Yao, Bangben; Chen, Xiujuan; Li, Weizhang; Song, Zhegang; Qin, Anjun; Sun, Jing; Tang, Ben Zhong

doi:10.1039/c5cc02138c

Cited by 46 publications

(23 citation statements)

References 36 publications

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“…Conjugated organic luminophors have wide applications in organic light-emitting diode (OLEDs)12345, smart materials678910 and sensors1112131415. Understanding the structure-property relationship is very important to guide the design of correct molecules for their providential applications1617181920212223.…”

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confidence: 99%

Anion-controlled dimer distance induced unique solid-state fluorescence of cyano substituted styrene pyridinium

Zhang

Kong

et al. 2016

Sci Rep

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Molecular packing arrangements play a key role in dominating the photophysical properties of luminophores in aggregated state but fine control of the molecular packing is a great challenge. This article describes a unique cyano substituted styrene pyridinium with interesting solid-state fluorescence that can be finely tuned by simple change of counteranions. The dilute solutions of the organic salts (PyCl, PyNO3, PyOTs and PyPh4B) exhibit very weak fluorescence. The crystals of the organic salts (PyCl, PyNO3, and PyOTs) show much enhanced fluorescence compared with their dilute solutions. It is interesting that the emissions changed from bluish-green to deep-blue and fluorescence quantum yields increase from 2.5% to 13.1% with the increasing of steric hindrance of the anions from chloridion, nitrate, to p-toluenesulfonate. Crystal and DFT studies reveal that the enhanced fluorescence is ascribed to the formation of dimers and bigger anions induce larger molecular separation in dimers. Tetraphenylboron anion with very large steric hindrance impedes the formation of dimers and thus results in non-fluorescent salt (PyPh4B). Meanwhile, this unique dimeric packing endows the crystal of PyNO3 with anisotropic fluorescence.

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confidence: 99%

Anion-controlled dimer distance induced unique solid-state fluorescence of cyano substituted styrene pyridinium

Zhang

Kong

et al. 2016

Sci Rep

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“…Several pyridinium-substituted TPE's derived from neutral precursors 2-5 (Fig. 1) have been found to possess interesting photoluminescent properties, 7,9,11,13 thus, TPVPs 6-8 were each converted to pyridinium salts to probe the effects of pyridinium ion formation on absorbance and emission in this system. Conversion of the neutral TPVP isomers 6-8 to the corresponding N-methyl pyridinium tetrauoroborate salts 9-11 was achieved in straightforward fashion upon treatment with [Me 3 O][BF 4 ].…”

Section: Resultsmentioning

confidence: 99%

“…11 Bis(4vinylpyridyl)TPE 4 has been used as monomer in construction of polycationic polymers for detection of heparin, 12 while the dimethylpyridinium salt displays interesting mechanochromic properties. 13 Finally, the tetra(4-pyridyl)TPE 5 has been employed in a number of AIE active constructs, including pH sensitive uorescence indicators 14 and supramolecular polymers. 15 TPE 5 also exhibits selective detection of Hg(HSO 4 ) 2 , 16 and has been demonstrated to be an excellent halogen bond acceptor in mediating assembly of crystalline uorescent halogen bonded networks with iodoarenes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and aggregation-induced emission properties of pyridine and pyridinium analogues of tetraphenylethylene

Gabr

Pigge

2015

RSC Adv.

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“…Furthermore, the well‐known aggregation‐induced emission (AIE) and crystallization‐induced emission enhancement (CIEE) phenomenon largely increases the possibility of exploring organic vapoluminescence materials with high solid‐state emission efficiency. To date, a variety of organic compounds incorporated 1,8‐naphthalimides (NPIs), tetraphenylethene (TPE), and squaraine have been well studied as vapoluminescent materials. In those materials, luminescent changes are generally depending on molecular sliding resulted from the cavities in crystalline lattices undiscerningly inserted by vapor molecules with suitable shape and size, thereby leads to a nonspecific detection ( Figure a).…”

Section: Introductionmentioning

confidence: 99%

Reversible Specific Vapoluminescence Behavior in Pure Organic Crystals through Hydrogen‐Bonding Docking Strategy

Xia

Jiang

Shen

et al. 2019

Advanced Optical Materials

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interactions (e. g., weak M-M interactions, metallophilic interactions, π-stacking, and coordination modes) in transition-metal assemblies can easily be perturbed with uptaking certain vapors into the crystal lattice, thereby inducing dramatic changes in emission color. [10][11][12][13][14][15][16][17][18] Moreover, relevant researches evidenced that isomer conversion of metal-complexes with remarkable emission color change can also be controlled through exposure to different vapor, which rendered a new approach to access great vapoluminescent materials. [19][20][21][22] Still and all, the metal-containing vapoluminescent compounds are generally expensive, difficult to synthesis, and environmentally unfriendly, thus limits their practical application.An alternative strategy is to construct pure organic vapoluminescent crystals by rational design, in viewing of their low cost, hypotoxicity, and molecular diversity. [23][24][25][26][27][28] Furthermore, the well-known aggregation-induced emission (AIE) [29][30][31] and crystallization-induced emission enhancement (CIEE) [32] phenomenon largely increases the possibility of exploring organic vapoluminescence materials with high solid-state emission efficiency. To date, a variety of organic compounds incorporated 1,8-naphthalimides (NPIs), [33,34] tetraphenylethene (TPE), [35][36][37] and squaraine [38][39][40] have been well studied as vapoluminescent materials. In those materials, luminescent changes are generally depending on molecular sliding resulted from the cavities in crystalline lattices undiscerningly inserted by vapor molecules with suitable shape and size, thereby leads to a nonspecific detection (Figure 1a). And also, there are very few examples of reversible luminescence change in organic crystal due to pseudopolymorphic transformations, such as solvation/desolvation and solvent exchange processes. Besides, some emissive porous organic frameworks have also emerged as vapoluminescence materials in viewing of their excellent gas adsorption property, but the results turned out to be unsatisfied. [41][42][43][44][45][46] As such, a novel design strategy for reversibly detecting specific vapor molecule in organic vapoluminescent materials is urgent desired and would prove beneficial to not only sensing, but also recording and biological applications. The design of vapoluminescence materials with high contrast, selectivity, and reversibility toward certain vapors is extremely attractive but remains a long-standing challenge. In this work, crystallization of squaraine dye (SQ) molecules in different solvents affords two organic crystals (R-SQ andSQ-2TFA) with the fluorescence quantum yield up to 0.81, which shows reversible phase transition of the crystals with different emission color via annealing treatment and solvent-vapor adsorption. From spectral and powder X-ray diffraction analysis, exposure of green-emitting R-SQ crystals to trifluoroacetic acid (TFA) vapor gives cyan-emitting SQ-2TFA crystals, while desorption of SQ-2TFA crystals by heating recovers R...

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Effect of ionic interaction on the mechanochromic properties of pyridinium modified tetraphenylethene

Abstract: Introducing ionic interaction into a soft tetraphenylethene-based AIE-molecule furnished the compound with robust mechanochromic effects while exhibiting aggregation-induced emission enhancement properties.

Cited by 46 publications

References 36 publications

Anion-controlled dimer distance induced unique solid-state fluorescence of cyano substituted styrene pyridinium

Anion-controlled dimer distance induced unique solid-state fluorescence of cyano substituted styrene pyridinium

Synthesis and aggregation-induced emission properties of pyridine and pyridinium analogues of tetraphenylethylene

Reversible Specific Vapoluminescence Behavior in Pure Organic Crystals through Hydrogen‐Bonding Docking Strategy

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