Organic solid fluorophores regulated by subtle structure modification: color-tunable and aggregation-induced emission

Zhang, Jing Nan; Kang, Hui; Li, Nan; Zhou, Shi-Gang; Sun, Hua; Yin, Shiwei; Zhao, Na; Tang, Ben Zhong

doi:10.1039/c6sc02875f

Cited by 167 publications

(88 citation statements)

References 52 publications

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“…1. 2-Styryl-substituted-6-methyl-4H-pyran-4-ylidene derivatives 4a, 4b, 4c, and 4e were obtained in "Fries rearrangement" of 3-cinnamoyl-substituted-4-hydroxy-6-methyl-2H-pyran-2ones 1a-d 14 and subsequent "Knoevenagel" condensation reactions 8,10 with malononitrile of the afforded 2-styryl-substituted-6-methyl-4H-pyran-4-ones 2a, 2b, 2c, and 2e. It is worth to mention that "Fries rearrangement" of 4-(3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-3-oxoprop-1-enyl)benzonitrile (1d) resulted in additional hydrolysis of cyano-group with further esterification in acidic conditions affording isobutyl 4-(2-(6-methyl-4-oxo-4H-pyran-2-yl)vinyl) benzoate (2e).…”

Section: Synthesis Of Dyesmentioning

confidence: 99%

“…Such a synthetic approach has been briefly introduced in Refs. 12 and 13 using 3-cinnamoyl-substituted-4-hydroxy-6-methyl-2H-pyrane-2-ones 14 as the starting reactants; however, other nonsymmetric bis-DCM or bis-DWK-type dyes so far to the best of our knowledge have not been reported. The approach used for the synthesis of nonsymmetric bis-DWK-dyes also enables the physical property tuning possibility through the incorporation of various functional groups within the 6-styryl-fragment.…”

Section: Introductionmentioning

confidence: 99%

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Glass-forming nonsymmetric DWK-dyes with 5,5,5-triphenylpentyl and piparazine moieties for light-amplification studies

et al. 2018

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A series of 2,6-bis-styryl-4H-pyran-4-ylidene fragment containing glass-forming organic compounds with bonded amorphous phase promoting bulky triphenyl moieties through piperazine structural fragment [2-(2-(4-(bis(2-(trityloxy)ethyl)amino)styryl)-6-methyl-4H-pyran-4ylidene)malononitrile derivatives (DWK)-T dyes] in a form of (5,5,5-triphenylpentyl)piperazin-1-yl)styryl)substituent attached to the 4H-pyran-4-yliden fragment in two-position have been synthesized and investigated as the potential light-amplification medium for organic solid-state lasers. DWK-T dye physical properties also depend on the structure of the other styryl-substituent attached to the 4H-pyran-4-ylidene backbone fragment in six-position. Thermal stability of synthesized dyes is above 312°C with the glass transitions from 97°C and up to 109°C. Obtained neat pure spin-cast films based on these compounds show photoluminescence with λ max in range from 672 to 695 nm, ASE λ max from 690 to 704 nm with ASE threshold values in range from 327 to 1091 μJ∕cm 2 , which are mostly influenced by the nature of the electron transition characteristics of various four substituents in a 6-styryl-fragment. The proposed synthetic approach could be useful for obtaining chemically stable and covalently bonded bulky triphenyl group containing glassy dyes, while the synthetic design allows to acquire different nonsymmetric 2,6-bis-styryl-4H-pyran-4ylidene fragment-containing compounds for red and infrared light-emitting and light amplification applications.

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Section: Synthesis Of Dyesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Glass-forming nonsymmetric DWK-dyes with 5,5,5-triphenylpentyl and piparazine moieties for light-amplification studies

et al. 2018

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“…This phenomenon is opposite to what occurs in many luminescent molecules in solution, whose fluorescence is quenched in the aggregate state owing to the formation of less luminous species such as excimers. [7] To date, a large number of AIE systems have been developed, such as tetraphenylethene (TPE) and its derivatives, [8][9][10][11][12][13] hexaphenylsilole (HPS) and its derivatives, [14] heterocyclic compounds containing Si, N, or P, [15][16][17] metal nanoclusters, [18][19][20] compounds containing rotational aromatic rings, [21] compounds containing BF 2 hexatomic ring [22][23][24][25][26][27][28] and others.…”

Section: Introductionmentioning

confidence: 99%

Potential‐Energy Surface and Dynamics Simulation of THBDBA: An Annulated Tetraphenylethene Derivative Combining Aggregation‐Induced Emission and Switch Behavior

et al. 2019

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Electronic structure calculations and nonadiabatic dynamics simulations were carried out on the excited state decay mechanism of a typical aggregation-induced emission (AIE)active molecule, 10,10',11,11'-tetrahydro-5,5'-bidibenzo[a,d][7] annulenylidene (THBDBA), which was experimentally found to be almost non-emissive in THF solution but highly luminescent as an aggregate. At the MS-CASPT2//CASSCF level, the decay path from S 1 leads to a conical intersection (CI) seam with the ground state (S 0 ) via a cyclization process of two neighboring phenyl groups. Nonadiabatic dynamics simulations of 367 surface hopping trajectories show that all the structures of hopping points resemble those of the S 1 /S 0 CI seam with cyclized geometry. The final structures of trajectories hopping to S 0 belong to either Franck-Condon (FC) like structures (66.8 %) or cyclized conformers (33.2 %), which agrees well with the experimental result of 23 % cyclization product (Y. Cai et al. Chem. Sci., 2011, 2, 2029-2034. Our results also indicate that long-time irradiation leads to a photostationary state where the open and cyclized forms interconvert photochemically. The preference for photocyclization over double bond isomerization is due to the rigidity of the dihydrofulvene rings. From the point of view of AIE, the calculations suggest that THBDBA follows our restricted access to a CI (RACI) model because the photocyclization requires large displacements of the phenyl rings. These displacements must be blocked in the aggregate phase, inhibiting the decay and leading to luminescence. Our study contributes to understand the AIE and switch behavior of THBDBA and will be useful to support the design of new molecules with these features.[a] Dr.

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“…To date, the majority of OCL materials are based on the aggregation‐induced‐emission (AIE) type fluorophores, an anti‐ACQ phenomenon, which are weak or practically nonfluorescent in solution, but become strong emitter in aggregated states. [3c,6] Although AIE materials exhibit their potential application in variety fields, it is desirable to develop the fluorescent materials that are strong emissive both in solution and solid state. Such materials usually display different fluorescent properties in their monomeric and aggregated states, and are beneficial for the molecular‐level understanding the relationship between the fluorescent properties and the molecular packing characteristics.…”

Section: Introductionmentioning

confidence: 99%

A Solid‐State Fluorescent Material Based on Carbazole‐Containing Difluoroboron β‐Diketonate: Multiple Chromisms, the Self‐Assembly Behavior, and Optical Waveguides

Chen

Zhang

Niu

et al. 2017

Adv Funct Materials

132

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A carbazole-containing difluoroboron β-diketonate complex (BCZ), which shows strong fluorescence in both the solid state and in organic solutions, is reported. The crystalline materials of BCZ obtained from different solvents display different emission colors. Single-crystal analysis reveals that the enhanced overlap between adjacent molecules induces increased excited-state delocalization and is responsible for the variation of the emission colors from yellow to red. The emission colors of the materials are effectively tuned by external stimuli such as grinding, heating, and solvent vapor. The powder X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, and 1 H NMR studies on materials of BCZ reveal that the thermochromic properties of BCZ are closely related to the removal of solvent molecules from the crystalline powders upon heating. Moreover, uniform 1D microstructures of BCZ obtained by solvent exchange in solution exhibit optical waveguide property with low optical loss.The ORCID identification number(s) for the author(s) of this article can be found under http://dx.

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Organic solid fluorophores regulated by subtle structure modification: color-tunable and aggregation-induced emission

Abstract: Organic solid fluorophores based on p-bis(2,2-dicyanovinyl)benzene were designed and synthesized, which displayed a tunable emission color and substituent dependent optical behavior.

Cited by 167 publications

References 52 publications

Glass-forming nonsymmetric DWK-dyes with 5,5,5-triphenylpentyl and piparazine moieties for light-amplification studies

Glass-forming nonsymmetric DWK-dyes with 5,5,5-triphenylpentyl and piparazine moieties for light-amplification studies

Potential‐Energy Surface and Dynamics Simulation of THBDBA: An Annulated Tetraphenylethene Derivative Combining Aggregation‐Induced Emission and Switch Behavior

A Solid‐State Fluorescent Material Based on Carbazole‐Containing Difluoroboron β‐Diketonate: Multiple Chromisms, the Self‐Assembly Behavior, and Optical Waveguides

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