3-Methoxythiophene-Based Indophenine Reaction Generating an Isomeric Dynamic Equilibrium System

Abstract

A 3-methoxythiophene-based indophenine reaction with N -(2-hexyldecyl)isatin in the presence of concentrated sulfuric acid produces an indophenine cis–trans isomeric dynamic equilibrium system, which is dominated by the (Z,E,Z) configuration with a trace of the (Z,Z,Z) configuration.

Synthesis and Study of Donor–Acceptor Conjugated Polymers via a Green Indophenine Polymerization Strategy

“…To circumvent isomerism in the synthesis of indophenine derivatives, it is advisible to opt for thiophene derivatives with steric substitutions. Indophenine reactions involving thiophene derivatives such as 3,4-propenedioxythiophene, 3,4-ethylenedioxythiophene, or 3,4-dimethoxythiophene can yield quinoidal conjugated indophenines having a specific configuration ( ZEZ ). , …”

“…To ensure stable charge transport under ambient conditions, the deep energy levels of LUMO and HOMO are very crucial. 32,33 Recently, there has been a significant focus on quinoidal molecular building blocks, including indophenine, thiophene-S,S-dioxidized indophenine (IDTO), 34,35 thieno [3,4-b]thiophene-indophenines (DTIPs), 36 methoxy quinoidal bithiophene (MQBt), 34 3,4-propylenedioxythiophene (ProDOT), 37 bis-quinoidal-3,4-ethylenedioxythiophene (bis-QEDOT), 38 3methoxythiophene-based indophenine (3MeT), 39 dal oligothiophenes, as promising semiconductors (Figure 1b). Polymers containing quinoidal molecular building blocks offer distinct advantages due to their highly planar arrangement.…”

“…Indophenine reactions involving thiophene derivatives such as 3,4-propenedioxythiophene, 3,4-ethylenedioxythiophene, or 3,4-dimethoxythiophene can yield quinoidal conjugated indophenines having a specific configuration (ZEZ). 34,39 Recently, we have reported fused bis-isatins and investigated their application in the indophenine reaction, 49 revealing synthesized polymers with potential for use in organic electronic devices. Encouraged by these results, we embarked on the synthesis of indophenine-based conjugated polymers.…”