Syntheses and optical, electrochemical, and photovoltaic properties of polymers with 6‐(2‐thienyl)‐4H‐thieno[2,3‐b]indole with a variety of electron‐deficient units

Abstract

Conjugated polymers were synthesized and used for polymer solar cells with new electron-rich units, 6-(2-thienyl)-4H-thieno [2,3-b]indole (2-TTI). 2-TTI was coupled with electron-pulling units, including benzothiadiazole and benzimidazole derivatives, to provide push-pull types of conjugated polymers (poly(8-(heptadecan-9-yl)-6-(thiophen-, and poly(8-(heptadecan-9-yl)-6-(thiophen-2-yl)-8H-thieno[2,3-b]indole)-alt-(2,2-dimethyl-5,6-bis(octyloxy)-4,7-di(thiophen-2-yl)-2H-benzimidazole) (PTTIDOMBI)). The synthesized conjugated polymers provided deep highest occupied molecular orbital energy levels for higher open-circuit voltages (V OC ). The device composed of PTTIDOMBI and [6,6]-Phenyl C 71 butyric acid methyl ester PC 71 BM (1:2) with chloronaphthalene additive showed a V OC of 0.72 V, a short-circuit current (J SC ) of 9.16 mA/cm 2 , and a fill factor of 0.43; this gave a power conversion efficiency (PCE) of 2.84%. The PTTIDOMBI provided better morphology for enhanced charge transport, and this led to the higher J SC and PCE of the organic solar cells.

Useful Access to Uncommon Thiazolo[3,2-a]indoles

“…The indole core fused with carbo or hetero rings constitutes a recurring framework of derivatives endowed with significant biological and medicinal properties and therefore subject of considerable attention . In this context, interesting examples are represented by the indole-annulated heterocycles containing sulfur atoms that display relevant properties such as antifungal, anticancer, anti-inflamatory, antihyperplasia, analgesic, antibacterial ones, antipsychotic activities or that were employed in the construction of small efficient push–pull chromophores . They are also found in several cruciferous phytoalexins, e.g., cyclobrassinin, spiro-brassinin, or brassicanal B, employed as plant defense chemicals .…”

Effect of titanium dioxide on the structural, thermal, and electrical properties of chlorinated natural rubber/poly (indole) blend nanocomposites for flexible nanoelectronic devices

“…Thus, the processability of PIN is an important factor to be addressed for better applicability in various fields. In the literature, PIN has been modified in a variety of ways, including the addition of substitute groups in the main chain, the synthesis of soluble precursors, the preparation of composites through chemical oxidation methods and the blending of PIN with one or more flexible and stable polymers 6–8 . Recent reports have shown that the fabrication of PIN composites by chemical oxidative polymerization methods has drawn much attention, due to its easy and effective nature 9 .…”

“…In the literature, PIN has been modified in a variety of ways, including the addition of substitute groups in the main chain, the synthesis of soluble precursors, the preparation of composites through chemical oxidation methods and the blending of PIN with one or more flexible and stable polymers. [6][7][8] Recent reports have shown that the fabrication of PIN composites by chemical oxidative polymerization methods has drawn much attention, due to its easy and effective nature. 9 This chemical oxidative method can also be used to increase the length of the polymer chain to the desired length.…”

A facile protocol for the preparation of 2-carboxylated thieno [2,3-b] indoles: a de novo access to alkaloid thienodolin

“…1). 5 A natural product worthy of particular attention is the thienodolin, an amido substituted thieno[2,3- b ]indole isolated from Streptomyces albogriseolus whose biological properties include plant–growth regulatory capacity and the nitric oxide synthase inhibition (Fig. 1).…”