Aggregation-Induced Emission of <i>cis</i>,<i>cis</i>-1,2,3,4-Tetraphenylbutadiene from Restricted Intramolecular Rotation

Chen, Junwu; Xu, Bin; Ouyang, Xiaoying; Tang, Ben Zhong; Cao, Yong

doi:10.1021/jp048475q

Cited by 269 publications

(156 citation statements)

References 32 publications

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“…13 CNMR (500 Hz, CDCl 3 ): d = 157. 4, 141.9, 141.5, 140.7, 139.4, 137.6, 133.0, 132.2, 130.8, 130.2, 130.0, 129.0, 128.8, 128.5, 128.4, 127.6, 127.1, 126.3, 125.2, 123.5, 120.4, 120.2, 118.7, 111.6, 110.1, 110.0 Crystallographic data for TPAN-C3:C 39 H 27 N 2 ,C 39 H 27 N 2 ,M = 522.62 gmol À1 ,T riclinic, a = 9.818(3), b = 12.379 (12) , c = 13.079 (13) ; b = 69.174(16) , V = 1437(2) 3, T = 293(2) K, R(int) = 0.0367, space group P À1 , D cal = 1.208 gcm…”

Section: Synthesis and Crystal Parametersmentioning

confidence: 99%

Highly Twisted Isomers of Triphenylacrylonitrile Derivatives with High Emission Efficiency and Mechanochromic Behavior

Sun

Qile

et al. 2016

ChemPhysChem

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Two novel triphenylacrylonitrile derivatives (TPAN‐C2 and TPAN‐C3) with highly twisted conformations have been successfully prepared by Suzuki coupling reaction. Both of them show mechanochromic (MC) fluorescent behaviour and exhibit remarkable fluorescence redshifts from sky‐blue to light green upon fully grinding them. Interestingly, the ground powders recover their original states upon heating at 100 °C for 1 min or fuming with solvents vapour. Such intriguing MC properties of TPAN‐C2 and TPAN‐C3 are attributed to their phase transitions between crystalline and amorphous states, which are confirmed by powder X‐ray diffraction (XRD) data. Moreover, the behaviour of both TPAN‐C2 and TPAN‐C3 indicates that the aggregation‐induced emission (AIE) gives rise to rather high fluorescence quantum efficiencies (Φf) of 0.78 and 0.97, respectively. The influences of stacking mode and molecular conformation on MC properties and the high Φf of TPAN‐C2 and TPAN‐C3 are discussed.

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Section: Synthesis and Crystal Parametersmentioning

confidence: 99%

Highly Twisted Isomers of Triphenylacrylonitrile Derivatives with High Emission Efficiency and Mechanochromic Behavior

Sun

Qile

et al. 2016

ChemPhysChem

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“…[52] 2,5-Diphenylsiloles have been known to be desilylated under basic conditions to produce the corresponding butadiene derivatives. [53][54][55][56] We initially considered the formation of cyclobutadienephlorin 11 (see below) and assumed that the macrocyclic constraints force the cyclobutadiene ring to close instead of the acyclic butadiene structure. Facile sil-A C H T U N G T R E N N U N G ylene extrusion was previously reported from 1,1-diarylsilacyclopropenes to afford the corresponding alkynes (thermal conditions) [57,58] and from 1,1-diamino-2,3-bis(trimethylsilyl)-silacyclopropene (photochemical conditions).…”

Section: Synthesis and Characterisation Of 21-silaporphyrinoidsmentioning

confidence: 99%

Reactivity of Silole within a Core‐Modified Porphyrin Environment: Synthesis of 21‐Silaphlorin and its Conversion to Carbacorrole

Skonieczny

Latos‐Grażyński

Szterenberg

2008

Chemistry A European J

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Condensation of 1,1-dimethyl-3,4-diphenyl-2,5-bis(p-tolylhydroxymethyl)silole with pyrrole and p-tolylaldehyde did not form the expected 21,21-dimethyl-2,3-diphenyl-5,10,15,20-tetra(p-tolyl)-21-silaporphyrin, but rather its reduced derivative, 21-silaphlorin, which contains a tetrahedrally hybridised C5 carbon atom. Attempts to trap 21-silaporphyrin resulted in the serendipitous discovery of a unique transformation of 21-silaphlorin into a non-aromatic isomer of 2,3-diphenyl-5,10,15,21-tetra(p-tolyl)-carbacorrole (iso-carbacorrole). This novel carbaporphyrinoid contains a cyclopentadiene ring embedded in a tripyrrolic framework. This transformation of 21-silaphlorin to iso-carbacorrole, carried out under oxidative conditions, involves extrusion of dimethylsilylene accompanied by migration of the C(meso)-(p-tolyl) unit to create a cyclopentadiene ring directly linked to the adjacent pyrrole through a tetrahedral carbon atom. Insertion of silver or copper ions into iso-carbacorrole gave two structurally related organometallic complexes of "true" carbacorrole in which the metal(III) ions are bound by three pyrrolic nitrogen atoms and a tetrahedrally hybridised C21 atom of the cyclopentadiene moiety. In the presence of oxygen, the silver(III) carbacorrole undergoes internal oxidation to 21-oxacorrole. The structure of silver(III) carbacorrole was determined by X-ray crystallography. The C21 atom was found to have a tetrahedral geometry. The Ag-C(sp(3)) (2.046(5) A) bond length is similar to that in silver(III) carbaporphyrinoids in which a trigonal carbon atom coordinates to the metal ion. Density functional theory was applied to model the molecular and electronic structure of 21-silaphlorin and feasible isomers of carbacorrole. The total energies (kcal mol(-1) vs. iso-carbacorrole), calculated at the B3LYP/6-31G(**)//B3LYP/6-31G(*) level for carbacorrole, iso-carbacorrole, vacataporphyrin and cyclobutadienephlorin, demonstrate the energetic preference for iso-carbacorrole.

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“…AIEgens in Type I are consisted of both aromatic rings and double bonds (CC, CN, NN, etc. ), such as tetraphenylethene (TPE), [4] distyrylanthracene, [5] imidazole-based analogues, [6] butadienes, [7] Schiff bases, [8] and cyano-substituted derivatives. [9] While in Type II, they are only consisted of aromatic rings, such as hexaphenylsilole (HPS), [3a,10] borondiiminates, [11] and tetraphenylpyrazine (TPP).…”

mentioning

confidence: 99%

Multifunctional AIEgens: Ready Synthesis, Tunable Emission, Mechanochromism, Mitochondrial, and Bacterial Imaging

Jiang

Kwok

et al. 2017

Adv Funct Materials

Self Cite

100

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Luminogens with aggregation-induced emission characteristics (AIEgens) are intriguing due to its rapid expansion in various high-tech applications. However, there is still in high demand on the development of novel AIEgens with easy preparation and functionalization, stable structures, tunable emissions, and high quantum efficiency. In this contribution, three AIEgens based on diphenyl isoquinolinium (IQ) derivatives are reported. They can be facilely synthesized and possess high structural stability, favorable visible light excitation, large Stokes shifts, high quantum yields, tunable colors, and sufficient two-photon absorption of near-infrared light. Importantly, they exhibit multifunctionalities. They exhibit mechanochromic property, making them capable to be applied for rewritable papers. They can also be applied in mitochondrial imaging with high specificity, cell permeability, brightness, biocompatibility, and photostability. They are promising for the applications in evaluation of mitochondrial membrane potential and image-guided cancer cell ablation. Last, they are able to stain bacteria in a wash-free manner. All these intriguing results suggest such readily accessible and multifunctional diphenyl IQ-based AIEgens provide a new platform for construction of advanced materials for practical applications.

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Aggregation-Induced Emission of cis,cis-1,2,3,4-Tetraphenylbutadiene from Restricted Intramolecular Rotation

Cited by 269 publications

References 32 publications

Highly Twisted Isomers of Triphenylacrylonitrile Derivatives with High Emission Efficiency and Mechanochromic Behavior

Highly Twisted Isomers of Triphenylacrylonitrile Derivatives with High Emission Efficiency and Mechanochromic Behavior

Reactivity of Silole within a Core‐Modified Porphyrin Environment: Synthesis of 21‐Silaphlorin and its Conversion to Carbacorrole

Multifunctional AIEgens: Ready Synthesis, Tunable Emission, Mechanochromism, Mitochondrial, and Bacterial Imaging

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