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Updated: Mar 27, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Core-Fluorinated Naphthalene Diimides: Synthesis, Characterization, and Application in n-Type Organic Field-Effect
Zhongyi Yuan1, Yingjie Ma1, Thomas Geßner2
1Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
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 cm(2) V(-1) s(-1).
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