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Conformationally Complex π‐Conjugated Molecular and Polymeric Materials: New Challenges for Organic Synthesis
Author(s) -
Guthrie Daryl A.,
Tovar John D.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900398
Subject(s) - conjugated system , reactivity (psychology) , organic molecules , regioselectivity , molecule , retrosynthetic analysis , group (periodic table) , organic synthesis , chemistry , protecting group , combinatorial chemistry , nanotechnology , halogenation , materials science , organic chemistry , polymer , alkyl , catalysis , total synthesis , medicine , alternative medicine , pathology
No protection? A unique, albeit fairly specialized, example of what promises to be a useful retrosynthetic consideration for those designing complex π‐molecular systems, namely, using conformation as a protecting group to shield a given reactive site in lieu of protecting‐group manipulation, is described (see scheme).Conformational influences profoundly impact the performance of organic electronic materials and the reactivity of organic molecules. We recently found that the expected former consideration was uniquely accompanied by the latter. This report describes a surprisingly regioselective bromination that suggests the general use of conformation as a protecting group during complex molecule synthesis.