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Synthesis 2011(15): 2387-2391  
DOI: 10.1055/s-0030-1260086
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Organic Halogenation Chemistry as a Vital Tool for the Construction of Functional π-Conjugated Materials

John D. Tovar*
Department of Chemistry and Department of Materials Science and Engineering, Johns Hopkins University, 3400 North Charles Street (NCB 316), Baltimore, MD 21218, USA
Fax: +1(410)5167077; e-Mail: tovar@jhu.edu;
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Publication History

Received 21 February 2011
Publication Date:
21 June 2011 (online)

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Abstract

Recent and ongoing efforts by the Tovar research group to exploit organic halogenation chemistry for the development of complex organic electronic materials are described. Standard synthetic approaches involving free-radical and electrophilic reaction pathways are presented along with strategies that use ionizable protons or triazenes as masking groups for aromatic halides. Forward synthetic processes that highlight the extended chemistry that can be applied to these halogenated substrates to give complex π-conjugated molecules are also discussed. The examples presented are specific to work from the group’s laboratories, but the halogenation procedures are sufficiently general to be suitable for use on many other conjugated frameworks.

Key words

electrophilic aromatic substitutions - free radicals - arenes - halogenation - conjugation