he molecular properties of benzothieno[3,2‐b]benzothiophene (BTBT) are vulnerable to the structural modifications which in turn are decided by the functionalization of the backbone. Hence versatile synthetic strategies are needed to discover the properties of this molecule. To address this, we have attempted heteroatom (oxygen) functionalization of BTBT by a concise and easily scalable synthesis. Four‐fold hydroxy substituted BTBT is the key intermediate, from which the compounds 2,3,7,8‐ bis(ethylenedioxy)‐benzothieno[3,2‐b]benzothiophene and 2,3,7,8‐ bis(methylenedioxy)‐benzothieno[3,2‐b]benzothiophene are synthesized. The difference in ether functionalities on the BTBT scaffold influences the ionisation potential values substantially. The crystal structure reveals the transformation of the herringbone motif in bare BTBT towards π stacked columns in the newly synthesized derivatives. The results are further elaborated with the aid of quantum chemical calculations.
- crystal structure data
- BTBT scaffold
Mohankumar, M., Chattopadhyay, B., Sanguinet, L., Kennedy, A. R., Lemaur, V., Cornil, J., ... Hadji, R. (2018). Oxacycle fused benzothieno[3,2‐b]benzothiophene derivatives: synthesis, electronic structure, electrochemical properties, ionisation potential, and crystal structure. ChemPlusChem. https://doi.org/10.1002/cplu.201800346