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Core-Fluorinated Naphthalene Diimides: Synthesis, Characterization, and Application in n-Type Organic Field-Effect Transistors

Author:
Yuan, Zhongyi, Ma, Yingjie, Geßner, Thomas, Li, Mengmeng, Chen, Long, Eustachi, Michael, Weitz, R. Thomas, Li, Chen, Müllen, Klaus
Source:
Organic letters 2016 v.18 no.3 pp. 456-459
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, dioxane, energy, halogens, naphthalene, transistors, vapors
Abstract:
A series of difluoro- and tetrafluoro-substituted naphthalene diimides (NDIs) were synthesized by halogen exchange reactions of corresponding bromo-NDIs with CsF in dioxane. Two strong electron acceptor molecules 6 and 8 with low-lying LUMO energy levels of −4.27 and −4.54 eV were obtained, starting from tetrafluoro-NDI. Organic field-effect transistors (OFETs) based on these fluorinated NDIs were fabricated by vapor deposition, exhibiting n-channel field-effect character under ambient conditions with the highest mobility of 0.1 cm² V–¹ s–¹.
Agid:
5792286