Issue 33, 2021

Effect of molecular geometry and extended conjugation on the performance of hydrogen-bonded semiconductors in organic thin-film field-effect transistors

Abstract

A general synthetic method has been used for the condensation of the 7-azaindole substructure at both extremes of centrosymmetric fused polyheteroaromatic systems. Four different aromatic spacers (benzene, naphthalene, anthracene and pyrene) that modify the molecular geometry and the π-conjugated surface have proved the ability of 7-azaindole to work as a building block that can control the crystal packing through reciprocal hydrogen bond interactions. Two possible self-assembled columnar arrangements have been observed as a result of the π–π interactions between hydrogen-bonded ribbon-like supramolecular structures. A detailed comparative analysis of the molecular organisation driven by hydrogen bonding and π-stacking, in combination with DFT calculations, has revealed an interesting evolution of the charge transport parameters. Organic thin-film field-effect transistors have been fabricated with the hydrogen-bonded semiconductors, reaching mobilities that demonstrate the potential of this supramolecular approach to control the molecular organisation and promote the electronic communication between the organic building blocks.

Graphical abstract: Effect of molecular geometry and extended conjugation on the performance of hydrogen-bonded semiconductors in organic thin-film field-effect transistors

Supplementary files

Article information

Article type
Paper
Submitted
23 mar 2021
Accepted
28 mai 2021
First published
28 mai 2021

J. Mater. Chem. C, 2021,9, 10819-10829

Effect of molecular geometry and extended conjugation on the performance of hydrogen-bonded semiconductors in organic thin-film field-effect transistors

P. Gómez, J. Cerdá, M. Más-Montoya, S. Georgakopoulos, I. da Silva, A. García, E. Ortí, J. Aragó and D. Curiel, J. Mater. Chem. C, 2021, 9, 10819 DOI: 10.1039/D1TC01328A

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