Premium
Cover Picture: Synthesis of opp ‐Dibenzohexaphyrins(1.1.1.1.1.1) by Retro‐Diels–Alder Reaction (Asian J. Org. Chem. 6/2014)
Author(s) -
Ishida Shinichiro,
Kuzuhara Daiki,
Yamada Hiroko,
Osuka Atsuhiro
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201490010
Subject(s) - rhodium , chemistry , metalation , stereochemistry , bicyclic molecule , oxidative addition , photochemistry , catalysis , medicinal chemistry , organic chemistry
opp ‐Bicyclo[2.2.2]octadiene‐fused hexaphyrins were transformed into opp ‐dibenzohexaphyrins under retro‐Diels‐Alder (rDA) reaction conditions. In their Full Paper on page 716 ff., Atsuhiro Osuka and co‐workers show that rigidifying the resulting framework by rhodium(I) metalation enabled the evaluation of the degree of conjugation expansion. Absorption profiles for the rhodium(I) complex were drastically red‐shifted in comparison to the parent complex. Such profound red‐shifts indicate that introducing fused benzene rings on to the periphery of the hex framework is a useful strategy for π‐network expansion. The rDA π‐expansion has been likened to blooming caliculi of the famous cherry blossom tree.