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Rational Monomer Design towards 2D Polymers: Synthesis of a Macrocycle with Three 1,8‐Anthrylene Units
Author(s) -
Kissel Patrick,
Schlüter A. Dieter,
Sakamoto Junji
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.200900781
Subject(s) - sonogashira coupling , monomer , relevance (law) , key (lock) , computer science , combinatorial chemistry , cycloaddition , chemistry , rational design , polymer , nanotechnology , catalysis , organic chemistry , materials science , political science , law , palladium , computer security
An iterative synthesis of a macrocycle with three 1,8‐anthrylene units (see picture, R=C 6 H 13 ) was achieved by using Pd‐catalyzed cross‐coupling protocols, in which a copper‐free Sonogashira reaction was the key to the final cyclization. Photochemical model reactions suggest that the macrocycle has the potential to undergo photo‐induced [4+4] cycloaddition without undesired side reactions, which is of relevance for the ultimate goal of creating 2D polymers.