A–π–D–π–A carbazole derivatives with remarkable solvatochromism and mechanoresponsive luminescence turn-on

Wen, Ping; Gao, Zhixiang; Zhang, Rong; Li, Anran; Zhang, Fang; Li, Jie; Xie, Jingjuan; Wu, Yuezhen; Wu, Min; Guo, Kunpeng

doi:10.1039/c7tc00559h

Cited by 114 publications

(42 citation statements)

References 47 publications

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“…The drastic decrease of Φ f in ACN can be ascribed to the strong solvation effect and higher probability of the ICT process in high-polarity solvent, leading to a fraction of non-emissive ICT state. This phenomenon has been already reported in earlier studies for the similar type of molecules 43 , 44 .…”

Section: Resultssupporting

confidence: 88%

Halogen-Bond-Assisted Photoluminescence Modulation in Carbazole-Based Emitter

Salunke

Durandin

Ruoko

et al. 2018

Sci Rep

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Halogen bonding between a carbazole-based, pyridine-substituted organic semiconductor and a common halogen-bond donor (pentafluoroiodobenzene) yields efficient halogen-bond-driven fluorescence modulation in solution. Steady-state, time-resolved emission and absorption spectroscopy as well as density functional theory studies demonstrate that the fluorescence modulation arises from halogen-bond-induced intramolecular charge transfer. Fluorescence modulation offers a range of possibilities both in solution and in the solid state, for instance providing a potential pathway for the design of tunable luminescent materials for light-emitting devices.

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Section: Resultssupporting

confidence: 88%

Halogen-Bond-Assisted Photoluminescence Modulation in Carbazole-Based Emitter

Salunke

Durandin

Ruoko

et al. 2018

Sci Rep

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“…Therefore, they usually reveal weak emission or are non-emissive in solution and emit enhanced uorescence in the solid state. 16 Thus, ICT dyes with AIEactive materials are expected to become a foundation for MFC materials. In order to achieve novel smart materials with multi-stimuli responsive characteristics, we designed and synthesized a new D-p-A type triphenylamine modied benzimidazole derivative TBM (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Reversible mechanofluorochromism and acidochromism using a cyanostyrylbenzimidazole derivative with aggregation-induced emission

et al. 2017

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“…However, it exhibited AIE property in aggregates (Figure b). In THF/H 2 O mixtures, the PL intensity was weak and slightly decreased when the water fraction was lower than 60% due to typical ICT effect arising from the increased solvent polarity through an increase in the water fraction, while it dramatically increased after the water content above 60% due to the formation of aggregates (Figures S3 and S4, Supporting Information) . The AIE‐active property of mSOAD may be ascribed to the physical restricted intramolecular rotation and reduced intermolecular interactions, by both of which the nonradiative decay of the excited state can be reduced .…”

Section: Resultsmentioning

confidence: 99%

Zig‐Zag Acridine/Sulfone Derivative with Aggregation‐Induced Emission and Enhanced Thermally Activated Delayed Fluorescence in Amorphous Phase for Highly Efficient Nondoped Blue Organic Light‐Emitting Diodes

Zhang

Wang

et al. 2018

Advanced Optical Materials

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weight, flexibility as well as low-cost device production for lighting and displaying applications. In the past decades, emissive materials that can harvest both singlet (25%) and triplet (75%) excitons have attracted significant interest. Followed the phosphorescent noblemetal complexes, thermally activated delayed fluorescent (TADF) materials were emerged and were considered as an important breakthrough. [1][2][3] This is because these purely organic emitters, as inexpensive alternatives, are able to convert excitons from the lowest triplet excited state (T 1 ) to the lowest singlet excited state (S 1 ) through reverse intersystem crossing (RISC), thus giving theoretical maximum internal electroluminescence quantum efficiency up to 100%. [4,5] Motivated by this, numerous TADF materials that comprise of electron donor (D) and electron acceptor (A) segments to yield charge transfer systems with a thermally accessible energy gap between S 1 and T 1 have been developed. [6][7][8][9][10] However, to meet the demand of high-quality singleand full-color OLEDs in practical applications, highly efficient blue TADF emitters are of great significance but still rare. [10][11][12][13][14][15][16] Moreover, despite a few important precedents with neglectable concentration quenching, [17,18] most of the reported blue TADF molecules that suffer from aggregationcaused quenching have to be applied in doped OLEDs, which challenged in precise control of the doping concentration, complicated structure, and expensive fabrication.To overcome this limitation, emissive materials with aggregation-induced emission (AIE) characteristics of which possess intense luminescence in the aggregated state become a promising strategy as emitting layers (EML) for efficient nondoped OLEDs. [19][20][21][22][23][24] In addition, to achieve high performance and good repeatability, the most efficient devices are still fabricated under thermal evaporation processing, in which the emissive materials are used in their amorphous phase. Therefore, several issues about the emissive materials are significant Luminescent materials simultaneously exhibiting aggregation-induced emission (AIE), superior luminous efficiency, and thermally activated delayed fluorescence (TADF) properties in amorphous phase are eagerly required for highly efficient nondoped organic light-emitting diodes. In this contribution, an acridine/sulfone derivative, bis(3-(9,9-dimethyl-9,10-dihydroacridine) phenyl)sulfone (mSOAD), designed and synthesized by combing a diphenylsulfone (DPS) core with bi-9,9-dimethyl-9,10-dihydroacridine (DMAC) substituted at the 3,3′-positions is demonstrated. The highly twisted zig-zag configuration endows the compound with desired frontier orbital distribution for extremely small energy gap between singlet and triplet states (ΔE ST = 0.02 eV) of TADF molecule and prominent AIE characteristic. More importantly, its amorphous sample displays enhanced quantum fluorescence yield as well as superior TADF characteristic, which exhibits advantage for device fabrica...

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A–π–D–π–A carbazole derivatives with remarkable solvatochromism and mechanoresponsive luminescence turn-on

Abstract: Two A–π–D–π–A carbazole derivatives differing in N-hexyl and N-isooctyl substituents were developed. They exhibited a prominent solvatochromic effect and luminescence turn-on characteristics under mechanical force stimuli.

Cited by 114 publications

References 47 publications

Halogen-Bond-Assisted Photoluminescence Modulation in Carbazole-Based Emitter

Halogen-Bond-Assisted Photoluminescence Modulation in Carbazole-Based Emitter

Reversible mechanofluorochromism and acidochromism using a cyanostyrylbenzimidazole derivative with aggregation-induced emission

Zig‐Zag Acridine/Sulfone Derivative with Aggregation‐Induced Emission and Enhanced Thermally Activated Delayed Fluorescence in Amorphous Phase for Highly Efficient Nondoped Blue Organic Light‐Emitting Diodes

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