Premium
N‐Fusion Reaction Sequence of Heptaphyrin(1.1.1.1.1.1.1): Singly, Doubly, and Quadruply N‐Fused Heptaphyrins
Author(s) -
Saito Shohei,
Osuka Atsuhiro
Publication year - 2006
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.200600671
Subject(s) - chemistry , yield (engineering) , fusion , sequence (biology) , crystallography , molecule , stereochemistry , fluorescence , materials science , physics , biochemistry , linguistics , philosophy , organic chemistry , metallurgy , quantum mechanics
Abstract meso ‐Heptakis(pentafluorophenyl) heptaphyrin(1.1.1.1.1.1.1) ( 1 ) was prepared by a stepwise route in 39 % yield and its unique N‐fusion reaction (NFR) sequence has been revealed; this reaction leads to singly‐, doubly‐, and quadruply N‐fused heptaphyrins ( 4 , 5 , and 6 ) in good yields. These transformations are facilitated by the inherent conformational distortion of 1 as well as the distorted, folded conformations of N‐fused heptaphyrins 4 and 5 . The proximate arrangement of the three pyrrole units in 6 allowed for the formation of the tripyrrolylboron(III) complexes 7 , 8 , and 9 with unique coordination features. Molecules 1 , 5 , and 9 were structurally characterized by X‐ray crystallography. In addition, the boron complexes 7 , 8 , and 9 displayed weak but distinct fluorescence in the near infrared region.