Thiadiazole Fused Indolo[2,3-<i>a</i>]carbazole Based Oligomers and Polymer

Balaji, G.; Shim, Wong Low; Parameswaran, Manoj; Valiyaveettil, Suresh

doi:10.1021/ol901806q

Cited by 33 publications

(17 citation statements)

References 41 publications

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“…[58] The more anodic value found for ( [67] Polymerization of (2,1-a)-IF is also observed along oxidation at fixed potential. For example, a deposit prepared by oxidation at 2 V for 180 s, removed from the electrolyte, rinsed in dichloromethane and studied in a new "monomer free" solution, presents the profile shown in Figure [25,75] In addition, poly-(2,1-a)-IF appears stable in a wide potential range, that is, between 0.67 and 2.4 V. Poly-(2,1-a)-IF is hence highly more stable than structurally related electrogenerated polymer such as poly-(1,2-b)-indenofuorene, poly-(1,2-b)-IF [67] or poly-fluorene, poly(F). [76] Indeed, poly-(1,2-b)-IF and poly(F) present stable p-doping processes between 0.75 and 1.76 V and between 0.97 and 1.5 V, respectively.…”

Section: A C H T U N G T R E N N U N Gmentioning

confidence: 99%

“…This onset potential difference between poly-(2,1-a)-IF and (2,1-a)-IF is consistent with an extended p-conjugation in poly-(2,1-a)-IF as previously observed for other electrogenerated p-conjugated polymers. [25,75] In addition, poly-(2,1-a)-IF appears stable in a wide potential range, that is, between 0.67 and 2.4 V. Poly-(2,1-a)-IF is hence highly more stable than structurally related electrogenerated polymer such as poly-(1,2-b)-indenofuorene, poly-(1,2-b)-IF [67] or poly-fluorene, poly(F). [76] Indeed, poly-(1,2-b)-IF and poly(F) present stable p-doping processes between 0.75 and 1.76 V and between 0.97 and 1.5 V, respectively.…”

Section: Synthesismentioning

confidence: 99%

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(2,1‐a)‐Indenofluorene Derivatives: Syntheses, X‐ray Structures, Optical and Electrochemical Properties

Thirion

Poriel

Rault‐Berthelot

et al. 2010

Chemistry A European J

112

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Two novel fluorophores based on the (2,1-a)-indenofluorenyl backbone, dispiro[fluorene-9,11'-indeno[2,1-a]fluorene-12',9''-fluorene], (2,1-a)-DSF-IF and 11,12-dihydroindeno[2,1-a]fluorene (2,1-a)-IF have been prepared through original and efficient synthetic approaches. After consideration of synthetic features, the structural, optical and electrochemical properties of these new blue/violet emitters have been studied in detail by a combined experimental and theoretical approach. The properties of the (2,1-a)-DSF-IF and (2,1-a)-IF are also compared to those of their corresponding positional isomers based on the (1,2-b)-indenofluorenyl backbone and those of related dispirofluorene heteroacenes.

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Section: A C H T U N G T R E N N U N Gmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

(2,1‐a)‐Indenofluorene Derivatives: Syntheses, X‐ray Structures, Optical and Electrochemical Properties

Thirion

Poriel

Rault‐Berthelot

et al. 2010

Chemistry A European J

112

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“…[ 12 ] Balaji et al reported the synthesis and electrochemical polymerization of thiadiazole fused IC derivatives ( 1 ). [ 13 ] The thiadiazole‐fused ICs were further modified with different substituents and fused rings. [ 14–16 ] Thiadiazole‐fused ICs have been successfully incorporated into the conjugated polymers.…”

Section: Introductionmentioning

confidence: 99%

Triazole‐fused indolo[2,3‐a]carbazoles: synthesis, structures, and properties

Ghosh

Das

Kumar

et al. 2020

Journal of Heterocyclic Chem

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The synthesis, structure, and photophysical and electrochemical properties of triazole fused indolo[2,3‐a]carbazole derivatives 2‐5 are reported. The key step involved in the synthesis of triazole fused indolo[2,3‐a]carbazole derivatives is the Cadogan ring closing reaction. 2‐Hexyl‐5,6‐dinitro‐2H‐benzo[d][1,2,3]triazoles having 4,7‐diaryl capping were subjected to the Cadogan cyclization reaction to obtain compounds 2‐5. In contrast to thiadiazole‐fused indolo[2,3‐a]carbazole 1, bromination of triazole‐fused indolo[2,3‐a]carbazole 4 afforded only meta‐dibrominated product with respect to the nitrogen of fused pyrrole rings on treatment with both N‐bromosuccinimide (NBS) and elemental bromine. These compounds showed positive solvatochromism in their emission spectra. Incorporation of electron‐donating substituent in the indole moiety resulted in the elevation of the highest occupied molecular orbital (HOMO) level. Density functional theory (DFT) calculations were performed to support the experimental findings.

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“…6-Bromo-4H-thieno[3,2-b]indole was synthesized according to the procedure of Dong and co-workers (Yang et al, 2017). Referring to the synthesis of indolocarbazole derivatives (Kato et al, 2012;Balaji et al, 2009), we designed a synthetic route (Fig. 2) and the detailed synthesis procedure of TIP is described below.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Synthesis and properties of a novel decacyclic S,N-heteroacene

Li¹,

Wang²,

Zhan³

et al. 2022

Acta Crystallogr C

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S,N-Heteroacene materials with fused multicyclic heteroaromatics have become increasingly attractive for organic optoelectronic device applications. In this work, the Cadogan ring-closure reaction between the benzene moiety of thieno[3,2-b]indole and 5,6-dinitrobenzo[c][1,2,5]thiadiazole was employed to prepare the novel decacyclic S,N-heteroacene 15,16-dibutyl-14,17-didodecyldithieno[2′′,3′′:2′,3′]indolo[6′,7′:4,5]pyrrolo[3,2-e:2′,3′-g][2,1,3]benzothiadiazole (TIP), C58H76N6S3. The conjugated backbone of TIP is extended in comparison with its octacyclic analogue as the central unit within Y6-type molecular acceptors, a family of overwhelming electron acceptors in polymer solar-cell research. The single-crystal X-ray diffraction (SC-XRD) characterization indicated the existence of π–π and C(sp 2)—H...π interactions among TIP molecules. The electrochemical and optical properties of TIP were also characterized. As a novel S,N-heteroacene building block, TIP is anticipated to be of potential use in the construction of promising electronic materials.

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Thiadiazole Fused Indolo[2,3-a]carbazole Based Oligomers and Polymer

Cited by 33 publications

References 41 publications

(2,1‐a)‐Indenofluorene Derivatives: Syntheses, X‐ray Structures, Optical and Electrochemical Properties

(2,1‐a)‐Indenofluorene Derivatives: Syntheses, X‐ray Structures, Optical and Electrochemical Properties

Triazole‐fused indolo[2,3‐a]carbazoles: synthesis, structures, and properties

Synthesis and properties of a novel decacyclic S,N-heteroacene

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