Extended benzodifuran–thiophene systems connected with azomethine junctions: synthesis and electronic properties

Moussallem, Chady; Gohier, Frédéric; Frère, Pierre

doi:10.1016/j.tetlet.2015.07.030

Cited by 17 publications

(8 citation statements)

References 33 publications

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“…For compound BDF2, the extension of the conjugation with the two furan cycles favours the access to the polycationic state. Thus, the first oxidation wave at E1 = 0.95 V corresponds to a direct access to the dication in a bi-electronic process while the oxidation to the trication radical is at E2 = 1.37 V. Recently similar results were obtained with extended benzofuranthiophene-TPA derivatives [49], indicating that the central benzodifuran moiety allows a perfect electronic delocalization. The experimental HOMO levels, calculated from the onset of the oxidation peak [50]( −5.6 eV for BDF1 and -5.5 eV for BDF2), follows the tendency given by the theoretical calculations with in particularly a small difference between the levels of BDF1 and BDF2 of only 0.1 eV.…”

Section: Resultssupporting

confidence: 63%

Facile synthesis and optical properties of extended TPA-Benzodifuran derivatives connected by cyano-vinylene junctions

2018

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Two new conjugated molecules based on triphenylaminebenzo [1,2-b:4,5-b']difuran moieties and integrating cyanovinyl bonds have been synthesized by using the new benzodifuran-acetonitrile synthon, easily and rapidly prepared in two steps from 2,2'-(2,5-dihydroxy-1,4-phenylene)diacetic acid. The electronic properties of the molecules were analysed by UV-Vis absorption and emission spectroscopies and cyclic voltammetry. The potential use of the molecules as donor materials for photovoltaic conversion were evaluated in simple bilayer solar cells using C60 as the acceptor materials. The comparison between the two derivatives reveals that the extension of the conjugated system with the insertion of furan cycles leads to a narrowing band gap, a better emission property, a direct access to dication state and an enhancement of the photovoltaic characteristics.

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Section: Resultssupporting

confidence: 63%

Facile synthesis and optical properties of extended TPA-Benzodifuran derivatives connected by cyano-vinylene junctions

2018

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“…Nowadays, much attention is devoted to organic semiconductor materials for organic electronic applications, such as organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), flexible light displays, flat panel displays, sensors, nonlinear materials, or field effect transistors (FETs) [1,2]. Organic compounds are characterized by many useful features, with the first perhaps being practically unlimited possibilities of chemical structure modifications for tuning their properties for particular applications and also the low cost of device production [1]. Among various small molecules synthesized for organic electronics, conjugated compounds containing imine bonds (-N=CH-) are known as Schiff bases or azomethines or imines.…”

Section: Introductionmentioning

confidence: 99%

Symmetrical and unsymmetrical azomethines with thiophene core: structure–properties investigations

et al. 2019

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Unsymmetrical and symmetrical azomethines were obtained using the condensation reaction of diamino-thiophene-3,4 dicarboxylic acid diethyl ester with 4-(1-pyrrolidino)benzaldehyde, fluorene-2-carboxaldehyde, 1-methylindole-3carboxaldehyde, and benzothiazole-2-carboxaldehyde. Their thermal, optical, and electrochemical properties were investigated, and the results were supported by calculations using the density functional theory. The studied compounds melted in the range of 170-260°C and can be converted into amorphous materials with high glass transition temperatures between 76 and 135°C. They were thermally stable up to 220-300°C. All imines were electrochemically active and exhibited low energy band gaps below 2 eV (except for one imine with E g = 2.39 eV) determined on the basis of cyclic voltammetry. Most of the azomethines were emissive in solution and in the solid state. Some of them showed both S 1 (first excited state) emission and S 2 (second excited state) emission or only fluorescence from higher excited state, which is first time observed for azomethines. The imine with the most promising properties was tested in a light-emitting diode, and its ability for emission of light under external voltage was demonstrated.

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“…But gold will glitter forever, researchers found that BDF‐based materials possessed high hole‐transporting performance, outstanding thermostability, and high luminescence quantum yields in the early 21st century. [ 218–222 ] Therefore, BDF‐based semiconductors have been widely applied to organic light‐emitting diodes (OLEDs), organic field‐effect transistors (OFETs), OSCs, etc. [ 49,223–228 ]…”

Section: Benzodichalcogenophene‐based Materials Used In Oscsmentioning

confidence: 99%

Recent Advances of Furan and Its Derivatives Based Semiconductor Materials for Organic Photovoltaics

Zheng

Huo

2021

Small Methods

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The state‐of‐the‐art bulk‐heterojunction (BHJ)‐type organic solar cells (OSCs) have exhibited power conversion efficiencies (PCEs) of exceeding 18%. Thereinto, thiophene and its fused‐ring derivatives play significant roles in facilitating the development of OSCs due to their excellent semiconducting natures. Furan as thiophene analogue, is a ubiquitous motif in naturally occurring organic compounds. Driven by the advantages of furan, such as less steric hindrance, good solubility, excellent stacking, strong rigidity and fluorescence, biomass derived fractions, more and more research groups focus on the furan‐based materials for using in OSCs in the past decade. To systematically understand the developments of furan‐based photovoltaic materials, the relationships between the molecular structures, optoelectronic properties, and photovoltaic performances for the furan‐based semiconductor materials including single furan, benzofuran, benzodifuran (BDF) (containing thienobenzofuran (TBF)), naphthodifurans (NDF), and polycyclic furan are summarized. Finally, the empirical regularities and perspectives of the development of this kind of new organic semiconductor materials are extracted.

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Extended benzodifuran–thiophene systems connected with azomethine junctions: synthesis and electronic properties

Cited by 17 publications

References 33 publications

Facile synthesis and optical properties of extended TPA-Benzodifuran derivatives connected by cyano-vinylene junctions

Facile synthesis and optical properties of extended TPA-Benzodifuran derivatives connected by cyano-vinylene junctions

Symmetrical and unsymmetrical azomethines with thiophene core: structure–properties investigations

Recent Advances of Furan and Its Derivatives Based Semiconductor Materials for Organic Photovoltaics

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