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Peripheral Functionalization of Subphthalocyanines
Author(s) -
GonzálezRodríguez David,
Torres Tomás
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801250
Subject(s) - chemistry , stille reaction , amination , borylation , combinatorial chemistry , molecule , surface modification , silyl ether , palladium , ether , coupling reaction , retrosynthetic analysis , catalysis , organic chemistry , nanotechnology , aryl , total synthesis , silylation , alkyl , materials science
The optimization of synthetic methodologies that lead to novel synthetically and electronically valuable SubPc molecules is of great interest for the use of these molecules in applied fields. In this work, we describe some useful procedures for the incorporation of diverse functional groups in the periphery of the SubPc macrocycle. Different metal‐catalyzed cross‐coupling reactions, including Stille or Suzuki couplings and palladium‐catalyzed borylation or amination reactions, have been optimized in order to obtain high yields and avoid SubPc decomposition. In addition, we report on the scope of the use of ether functionalities in the condensation reaction with BCl 3 and on the synthesis of a trihydroxySubPc, a very valuable compound that could be obtained by deprotection of a silyloxy‐SubPc precursor. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)