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

Zhongyi Yuan; Yingjie Ma; Thomas Geßner; Mengmeng Li; Long Chen; Michael Eustachi; R Thomas Weitz; Chen Li; Klaus Müllen

doi:10.1021/acs.orglett.5b03489

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

Org Lett. 2016 Feb 5;18(3):456-9. doi: 10.1021/acs.orglett.5b03489. Epub 2016 Jan 14.

Authors

Zhongyi Yuan¹, Yingjie Ma¹, Thomas Geßner², Mengmeng Li¹, Long Chen¹, Michael Eustachi², R Thomas Weitz², Chen Li¹, Klaus Müllen¹

Affiliations

¹ Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
² BASF SE, 67056 Ludwigshafen, Germany.

PMID: 26763673
DOI: 10.1021/acs.orglett.5b03489

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).

Publication types

Research Support, Non-U.S. Gov't