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

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 tr...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-09, Vol.22 (38), p.13643-13652
Main Authors: de la Peña, Alejandro, Arrechea-Marcos, Iratxe, Mancheño, María J., Ruiz Delgado, M. Carmen, López Navarrete, J. Teodomiro, Segura, José L., Ponce Ortiz, Rocío
Format: Article
Language:English
Subjects:
Assemblies
Chains
charge transfer
Chemistry
Derivatives
Field effect transistors
heterocycles
Inversions
Joints
Molecular orbitals
organic semiconductors
Semiconductor devices
spectroscopy
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Summary: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. Link's awakening: Inversion of the connections of the amidine linkers combined with controlled oligothiophene chain catenation in oligothiophene–naphthalimide assemblies provide an efficient method to tune the HOMO and LUMO energy levels, thus promoting ambipolarity in field‐effect transistors.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201602082