Synthesis and Characterization of 5,10-Bis(2-thienyl)indeno[2,1-a]indene Derivatives:  The First Examples of Conducting Polymers Containing a Rigid Bis(thienyl)butadiene Core

Abstract

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Synthesis and Reactions of Dibenzo[a,e]pentalenes

“…The key starting compound was diphenylsuccindanedione 2 [13][14][15], which was synthesized from diphenylsuccinic acid. Treatment of 2 with phenylmagnesium bromide and p-tolylmagnesium bromide followed by an addition of ammonium chloride afforded the corresponding diols 3a and 3b, respectively (Scheme 1) [12].…”

“…Starting from diketone 2, thienyl-substituted dibenzopentalenes were synthesized by the classical method (Scheme 27) [15]. Diketone 2 reacted with thienyllithium or thienylmagnesium bromide to afford the corresponding adducts, which were treated with acid to provide thienyl-substituted dibenzopentalenes 1ac-1ae.…”

“…When a cyclic voltammetric analysis of 1ac was carried out, the growth of a new redox system was observed upon scanning between 1.0 and 1.2 V and the electrode was modified, suggesting polymerization of 1ac on the electrode. The anodic study of the modified electrode between 1.0 and 1.5 V revealed that the original species on the modified electrode was further modified, perhaps due to intramolecular cyclization or polymerization through the benzene moiety (Scheme 28) [15]. The band gap of the resulting polymer was estimated to be about 2.2 V. …”

Synthesis of Functionalized 1H-Indenes and Benzofulvenes through Iodocyclization of o-(Alkynyl)styrenes

“…These molecules are present in the structure of many biologically active compounds [1][2][3][4] and they have also found application in material chemistry [5][6][7][8][9] and as ligands in metal catalysis. [10][11] Therefore, several approaches for the synthesis of 1H-indenes and benzofulvenes have been described.…”

Dithieno[a,e]pentalene Based Conjugated Polymers: Synthesis and Characterization

“…[25][26][27] Some pentalene derivatives such as dibenzopentalenes have been perceived as useful building blocks for synthesis of conjugated polymers because of their rigid planar and conjugated structure. [28][29][30][31][32] Small molecules based on dibenzopentalenes have been synthesized and applied in organic electronic devices. [31] Substituted dithieno[a,e]pentalenes (DTPs) are stable compounds and the efficient synthetic methods for them have been developed lately.…”