Synthesis of carbazole-based hetero-core-modified porphyrins

Cu(I)-mediated annulation reaction of a 1,1'-(1,3-butadiyne)-8,8'-(2,5-thiophene)-bridged carbazole dimer 10 with amines provided the N-substituted carbazole-based isophlorines 11a-11c. A similar annulation reaction with selenium in the presence of hydrazine monohydrate afforded hetero-cor...

Full description

Saved in:
Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 12; no. 17; pp. 2656 - 2662
Main Authors Maeda, Chihiro, Masuda, Motoki, Yoshioka, Naoki
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.05.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTES
ENEDIYNES
EXPANDED PORPHYRINS
FUSED PORPHYRINOIDS
NONPLANAR
STATE
CYCLIZATION
Online AccessGet full text

Cover

More Information
Summary:Cu(I)-mediated annulation reaction of a 1,1'-(1,3-butadiyne)-8,8'-(2,5-thiophene)-bridged carbazole dimer 10 with amines provided the N-substituted carbazole-based isophlorines 11a-11c. A similar annulation reaction with selenium in the presence of hydrazine monohydrate afforded hetero-core-modified isophlorine 12. The oxidation of 12 generated the corresponding 21-selena-23-thiaporphyrin 13, which exhibited NIR absorption. The intramolecular charge transfer from Se to S was confirmed by the H-1 NMR results along with DFT calculations.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob42564a