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Molecular and Electronic‐Structure Basis of the Ambipolar Behavior of Naphthalimide–Terthiophene Derivatives: Implementation in Organic Field‐Effect Transistors
Author(s) -
Ponce Ortiz Rocío,
Herrera Helena,
Mancheño María J.,
Seoane Carlos,
Segura José L.,
Mayorga Burrezo Paula,
Casado Juan,
López Navarrete J. Teodomiro,
Facchetti Antonio,
Marks Tobin J.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301489
Subject(s) - ambipolar diffusion , terthiophene , organic semiconductor , planar , field effect transistor , transistor , materials science , crystallinity , semiconductor , chemical physics , optoelectronics , computational chemistry , chemistry , electron , molecule , crystallography , organic chemistry , physics , computer graphics (images) , quantum mechanics , voltage , computer science
Abstract A new family of naphthalimide‐fused thienopyrazine derivatives for ambipolar charge transport in organic field‐effect transistors is presented. Their electronic and molecular structures were elucidated through optical and vibrational spectroscopy aided by DFT calculations. The results indicate that these compounds have completely planar molecular skeletons which promote good film crystallinity and low reorganization energies for both electron and hole transport. Their performance in organic field‐effect transistors is compared with twisted and planar naphthaleneamidine monoimide‐fused terthiophenes in order to understand the origin of ambipolarity in this new series of molecular semiconductors.