Pro-aromatic bisphenaleno-thieno[3,2-b]thiophene versus anti-aromatic bisindeno-thieno[3,2-b]thiophene: different ground-state properties and applications in field-effect transistors

Abstract

A pro-aromatic molecule BPT-TIPS displayed different ground-state electronic structure and physical properties from its anti-aromatic counterpart S2-TIPS.

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…A unique example of an extended phenalene containing an ortho -fused heterocycle is the pro-aromatic bisphenaleno-thieno[3,2- b ]thiophene ( 182.3 ) reported by Kim and Chi et al in 2015 ( Scheme 182 ). 360 It was synthesized from diacid 182.1 , which was converted into the corresponding acyl chloride and subjected to double Friedel–Crafts acylation, to afford the desired diketone 182.2 in 85% yield. Addition of triisopropylsilyl ethynyl lithium to 182.2 , followed by SnCl 2 reduction, gave the target 182.3 in 45% yield.…”

Indandione‐Terminated Quinoids: Facile Synthesis by Alkoxide‐Mediated Rearrangement Reaction and Semiconducting Properties

“…However, their termini are difficult to functionalize, and they are known to be as important as the quinoidal core in regulating the electronic properties of these compounds . Another type of quinoidal compounds is end capped by the aryl groups,– and they can be synthesized by nucleophilic addition to a carbonyl group with subsequent reduction (Figure b). The terminal aryl groups of the resulting compounds can serve as handles for the construction of quinoidal compounds with modifiable termini.…”

Synthesis of some mono and dialkynyl derivatives containing thieno[3,2-b]thiophene ring via Sonogashira alkynylation reaction

“…IR (cm -1 , KBr): 3057, 2930, 2852, 1730, 1590, 1487. 1 H NMR (CDCl3, 500 MHz) (ppm): 7.98 (dd, J = 7.5, 1.5 Hz, 1H),7.94 (dd, J = 7.5, 2.0 Hz, 1H),7.83 (dd, J = 8.0, 1.5 Hz, 1H),7.59 -7.50 (m,4H),7.43 (s, 1H), 7.21 (d, J = 8.0 Hz, 1H),7.28 (t, J = 7.5 Hz, 1H),7.20 (d, J = 7.5 Hz, 1H), 2.38 (s, 3H); 13…”

“…Thieno [3,2b]thiophene is a stable and electron-rich π-conjugated core with four carbon atoms that is a useful building block for the construction of organic semiconductors with different conjugation lengths by extending the conjugation length. Shi et al reported Sn-TIPS as a new high performance semiconductor; Figure 1 (left) [1]. [3,2-b]thiophene BPT-TIPS [1] andPd-catalyzed cross-coupling reactions of sp 2 -C halides with terminal acetylenes and Outline of the reaction scheme for Pd-Cu catalyzed cross-coupling of sp 2 -C halides with terminal acetylenes [2].…”

“…Shi et al reported Sn-TIPS as a new high performance semiconductor; Figure 1 (left) [1]. [3,2-b]thiophene BPT-TIPS [1] andPd-catalyzed cross-coupling reactions of sp 2 -C halides with terminal acetylenes and Outline of the reaction scheme for Pd-Cu catalyzed cross-coupling of sp 2 -C halides with terminal acetylenes [2].…”