Work

Modulating Electrochemical and Optical Properties of Oligothiophenes via Subtle Changes in Donnor ‐ Acceptor Sequence

Year: 2025

Type: article

Abstract: This study explores the synthesis and electronic properties of oligothiophenes derived from the 3‐hexyloxy‐4‐cyanothiophene building block. By exploiting the differential reactivity of thiophene's α‐positions, regioisomeric derivatives were synthesized with varying donor–acceptor sequences. These derivatives displayed distinct optical and electrochemical characteristics based on the relative positions of cyano acceptor and hexyloxy donor groups. Spectroscopic, computational, and electrochemical analyses revealed that substituent placement critically affects electronic properties, such as HOMO‐LUMO levels and band gaps. The introduction of alkoxy groups at external β‐sites promoted coupling reactions upon oxidation, leading to polymerization or dimerization. Conversely, cyano groups at these positions stabilized radical cations and dications, suppressing further reactions. These findings offer insights into designing conjugated systems with tunable properties, emphasizing the importance of substituent positioning for optimizing performance.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202500120

Authors: Savitha Gurunatham, Chady Moussallem, Frédéric Gohier, Pierre Frère

Institutions: Centre National de la Recherche Scientifique, Institut des Sciences et Technologies Moléculaires d'Angers, Université d'Angers, Lebanese University, Lebanese German University

Language: English

Topic: Organic Electronics and Photovoltaics

Subfield: Electrical and Electronic Engineering

Field: Engineering

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,330

OpenAlex ID: W4407840642

FWCI: 0.231

Cites: 37

Cited by: 1

Related to: 10