Tuning of the Electronic Levels of Oligothiophene-Naphthalimide Assemblies by Chemical Modification

Alejandro de la Peña; Iratxe Arrechea-Marcos; María J Mancheño; M Carmen Ruiz Delgado; J Teodomiro López Navarrete; José L Segura; Rocío Ponce Ortiz

doi:10.1002/chem.201602082

Tuning of the Electronic Levels of Oligothiophene-Naphthalimide Assemblies by Chemical Modification

Chemistry. 2016 Sep 12;22(38):13643-52. doi: 10.1002/chem.201602082. Epub 2016 Jul 19.

Authors

Alejandro de la Peña¹, Iratxe Arrechea-Marcos², María J Mancheño¹, M Carmen Ruiz Delgado², J Teodomiro López Navarrete³, José L Segura⁴, Rocío Ponce Ortiz⁵

Affiliations

¹ Department of Organic Chemistry, Faculty of Chemistry, Complutense University of Madrid, Madrid, 28040, Spain.
² Departament of Physical Chemistry, University of Malaga, Malaga, 29071, Spain.
³ Departament of Physical Chemistry, University of Malaga, Malaga, 29071, Spain. teodomiro@uma.es.
⁴ Department of Organic Chemistry, Faculty of Chemistry, Complutense University of Madrid, Madrid, 28040, Spain. segura@ucm.es.
⁵ Departament of Physical Chemistry, University of Malaga, Malaga, 29071, Spain. rocioponce@uma.es.

PMID: 27430480
DOI: 10.1002/chem.201602082

Abstract

Inversion of the connections of amidine linkers combined with controlled oligothiophene chain catenation in oligothiophene-naphthalimide assemblies provides an efficient method to tune the HOMO and LUMO values in this type of assemblies. This modification also suppresses the intramolecular charge transfer (ICT) band normally found in this type of derivatives, also delocalizing the frontier molecular orbitals over the whole conjugated skeleton. The resultant assemblies were used in the fabrication of field-effect transistors, which showed well-balanced ambipolar transport.

Keywords: charge transfer; field-effect transistors; heterocycles; organic semiconductors; spectroscopy.