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Unraveling the unusual effect of fluorination on crystal packing in organic semiconductorстатья Исследовательская статья
Статья опубликована в высокорейтинговом журнале
Статья опубликована в журнале из списка Web of Science и/или Scopus- Авторы: Ekaterina Komissarova, Dmitry Dominsky, Vladimir Zhulanov, Abashev George G., Afzal Siddiqui, Surya Prakash Singh, Andrey Yurievich Sosorev, Dmitry Paraschuk
- Журнал: Physical Chemistry Chemical Physics
- Год издания: 2019
- Издательство: Royal Society of Chemistry
- Местоположение издательства: United Kingdom
- DOI: 10.1039/C9CP05455C
- Аннотация: Owing to combination of chemical and thermal stability, favorable molecular packing, and efficient electron transport, naphthalene diimide derivatives (NDIs) are promising materials for n-channel organic field effect transistors (OFETs). For tuning the properties of n-conductive organic semiconductors, as well as for improvement of their air stability, fluorination is a frequently used approach. In this study, we demonstrate how very small modification of the molecular structure — fluorine substitution in p-position of the phenyl rings of N, N’-diphenyl-NDI (Ph NDI) — dramatically changes the crystal packing but almost does not affect charge transport. We show that this two-atom modification of Ph-NDI changes the molecular packing motif from π-stacking to herringbone one, in contrast with usually observed improvement of π-stacking with fluorination. This unexpected behavior is mainly attributed to changes in the electrostatic potential of the phenyl rings as a result of fluorination, which alters their relative orientation and modifies packing of the NDI cores. Nevertheless, though the herringbone packing is typically considered as less favorable for charge transport, the theoretical charge mobility is slightly higher in the fluorinated Ph-NDI. The results obtained improve the understanding of the relationship between the molecular and crystal structures of organic semiconductors and their impact on charge transport, which is of key importance for rational design of high-mobility materials for organic electronics.
- Добавил в систему: Доминский Дмитрий Игоревич