Effects of Odd–Even Side Chain Length of Alkyl-Substituted Diphenylbithiophenes on First Monolayer Thin Film Packing Structure

Hylke B. Akkerman, Stefan C. B. Mannsfeld, Ananth P. Kaushik, Eric Verploegen, Luc Burnier, Arjan P. Zoombelt, Jonathan D. Saathoff, Sanghyun Hong, Sule Atahan-Evrenk, Xueliang Liu, Alán Aspuru-Guzik, Michael F. Toney, Paulette Clancy, Zhenan Bao

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

Because of their preferential two-dimensional layer-by-layer growth in thin films, 5,5′bis(4-alkylphenyl)-2,2′-bithiophenes (P2TPs) are model compounds for studying the effects of systematic chemical structure variations on thin-film structure and morphology, which in turn, impact the charge transport in organic field-effect transistors. For the first time, we observed, by grazing incidence X-ray diffraction (GIXD), a strong change in molecular tilt angle in a monolayer of P2TP, depending on whether the alkyl chain on the P2TP molecules was of odd or even length. The monolayers were deposited on densely packed ultrasmooth self-assembled alkane silane modified SiO2 surfaces. Our work shows that a subtle change in molecular structure can have a significant impact on the molecular packing structure in thin film, which in turn, will have a strong impact on charge transport of organic semiconductors. This was verified by quantum-chemical calculations that predict a corresponding odd-even effect in the strength of the intermolecular electronic coupling. © 2013 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)11006-11014
Number of pages9
JournalJournal of the American Chemical Society
Volume135
Issue number30
DOIs
StatePublished - Jul 22 2013
Externally publishedYes

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