Structure and electronic properties of triphenylamine-substituted indolo[3,2-b]carbazole derivatives as hole-transporting materials for organic light-emitting diodes

Zhao, Huihui; Tao, Xutang; Wang, Fu-Zhi; Ren, Yan; Sun, Xueqin; Yang, Jiaxiang; Yan, Yun-Xing; Zou, Dechun; Zhao, Xian; Jiang, Minhua

doi:10.1016/j.cplett.2007.03.074

Cited by 66 publications

(17 citation statements)

References 19 publications

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“…Indolo [3,2-b]-carbazoles (ICZs) with different substitution patterns and polymers thereof have been investigated for use in organic electronic applications such as organic field effect transistors (OFETs) (25)(26)(27)(28)(29), organic light-emitting diodes (OLEDs) (30)(31)(32)(33), organic photovoltaics (OPVs) (34)(35)(36) and dye-sensitized solar cells (DSSCs) (37). We recently reported a short and high yielding alternative route toward 2,8-difunctionalized indolo [3,2b]carbazole which has demonstrated to be a versatile building block (38).…”

Section: Introductionmentioning

confidence: 99%

Improved Spectral Coverage and Fluorescence Quenching in Donor–acceptor Systems Involving Indolo[3‐2‐b]carbazole and Boron‐dipyrromethene or Diketopyrrolopyrrole

Khetubol

Snick

Clark

et al. 2015

Photochem & Photobiology

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A novel π-conjugated triad and a polymer incorporating indolo[3,2-b]-carbazole (ICZ) and 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) were synthesized via a Sonogashira coupling. Compared to the parent BODIPY the absorption and fluorescence spectrum were for both compounds broader and redshifted. The redshift of the fluorescence and the decrease of the fluorescence quantum yield and decay time upon increasing solvent polarity were attributed to the formation of a partial charge-transfer state. Upon excitation in the ICZ absorption band the ICZ fluorescence was quenched in both compounds mainly due to energy transfer to the BODIPY moiety. In a similar ICZ-π-DPP polymer (where DPP is diketopyrrolopyrrole), a smaller redshift of the absorption and fluorescence spectra compared to the parent DPP was observed. A less efficient quenching of the ICZ fluorescence in the ICZ-π-DPP polymer could be related to the unfavorable orientation of the transition dipoles of ICZ and DPP. The rate constant for energy transfer was for all compounds an order of magnitude smaller than predicted by Förster theory. While in a solid film of the triad a further redshift of the absorption maximum of nearly 100 nm was observed, no such shift was observed for the ICZ-π-BODIPY polymer.

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Section: Introductionmentioning

confidence: 99%

Improved Spectral Coverage and Fluorescence Quenching in Donor–acceptor Systems Involving Indolo[3‐2‐b]carbazole and Boron‐dipyrromethene or Diketopyrrolopyrrole

Khetubol

Snick

Clark

et al. 2015

Photochem & Photobiology

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“…Here we investigate voltage-induced fluorescence quenching in poly{5,11-di-2,3-epoxypropyl-6-pentyl-5,11-dihydroindolyl [3,2-b]carbazolyl-alt-4,4 0 -tiobisbenzentiole} (PIC) [20]. This material belongs to indolo [3,2-b]carbazole-based derivatives, which show good hole-transport properties [21][22][23][24][25][26] and are environmentally stable [21,22,27]. Quite successful attempts to use these materials in organic light-emitting diodes [27] and in field-effect transistors [28] were reported.…”

Section: Introductionmentioning

confidence: 99%

Fluorescence quenching by charge carriers in indolo[3,2-b]carbazole-based polymer

Karpicz¹,

Kirkus

Gražulevičius

et al. 2010

Journal of Luminescence

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“…In general, more hindered substrates react with diminished E / Z selectivities (entries Table 1 44 . Moreover, recently, their application has been expanded to the areas of molecular imaging and material chemistry 45,46 . As demonstrated, for instance, compound 3m can be effi ciently transformed to furocarbazole S5 through a photoelectronic cyclization-photoinduced decarboxylation cascade ( Fig.…”

Section: Resultsmentioning

confidence: 99%

Direct stereoselective α-arylation of unmodified enals using an organocatalytic cross-coupling-like reaction

Song

Zhang

et al. 2011

Nat Commun

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Cross-coupling reactions typically rely on the use of transition metal catalysis. However, although achieving this process using metal-free organocatalysts is highly challenging, it could offer unique opportunities to discover novel bond-forming strategies in organic synthesis. Here we report a new amine catalysed direct stereoselective C-H α -arylation reaction of unmodifi ed enals with bromoarenes. The power of this process, which involves an unprecedented iminiumMichael-alkylation-enamine-retro-Michael cascade sequence, has been demonstrated in the context of direct α -functionalization reactions of simple, unmodifi ed enals with 4-bromophenols, 1-bromo-2-naphthol and 3-bromoindoles under mild reaction conditions. Notably, the process can be used for highly stereoselective syntheses of non-readily accessible E isomers, which normally require the use of transition metal-promoted cross-couplings and functionalized enals. The results of these studies signifi cantly expand the scope of aminocatalysis.

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Structure and electronic properties of triphenylamine-substituted indolo[3,2-b]carbazole derivatives as hole-transporting materials for organic light-emitting diodes

Cited by 66 publications

References 19 publications

Improved Spectral Coverage and Fluorescence Quenching in Donor–acceptor Systems Involving Indolo[3‐2‐b]carbazole and Boron‐dipyrromethene or Diketopyrrolopyrrole

Improved Spectral Coverage and Fluorescence Quenching in Donor–acceptor Systems Involving Indolo[3‐2‐b]carbazole and Boron‐dipyrromethene or Diketopyrrolopyrrole

Fluorescence quenching by charge carriers in indolo[3,2-b]carbazole-based polymer

Direct stereoselective α-arylation of unmodified enals using an organocatalytic cross-coupling-like reaction

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