Topological Control of Paratropicity via Alternative Ring Fusion in Indacenodithiophene Isomers.

Authors

Anjana Ranasinghe Meegasmullage, Muhammad Usama Gul Khan, Jacob Mensah, Sean Parkin, Alice E Bruce, Mitchell R M Bruce, Judy I Wu, Tomas Marangoni

Published in

The Journal of organic chemistry. Jul 12, 2026. Epub Jul 12, 2026.

Abstract

We report the synthesis and characterization of a series of isomeric indacenodithiophenes (iso-IDTs) bearing various ethynyl substituents at the apical carbons. Absorption spectroscopy, cyclic voltammetry, and density functional theory (DFT) calculations were performed to investigate the electronic properties of these compounds. Notably, analogues with reduced steric protection (i.e., trimethylsilyl, adamantyl) were also successfully isolated and investigated. Computed nucleus-independent chemical shifts and ring current plot analyses reveal that iso-IDTs display reduced antiaromatic character compared to indenofluorene (IF) and the previously reported syn- and anti-fused IDT isomers, suggesting that the π-bond arrangement within the indacenodithiophene π-system can be leveraged for tuning their optoelectronic properties.

PMID:
42437356
Bibliographic data and abstract were imported from PubMed on 12 Jul 2026.

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