Synthesis of carbazole-based hetero-core-modified porphyrins

Chihiro Maeda; Motoki Masuda; Naoki Yoshioka

doi:10.1039/c3ob42564a

Synthesis of carbazole-based hetero-core-modified porphyrins

Chihiro Maeda, Motoki Masuda, Naoki Yoshioka

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

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 ¹H NMR results along with DFT calculations. This journal is

Original language	English
Pages (from-to)	2656-2662
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	17
DOIs	https://doi.org/10.1039/c3ob42564a
Publication status	Published - 2014 May 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/c3ob42564a

Cite this

@article{087dde93fd7f492e93275e48f0051059,

title = "Synthesis of carbazole-based hetero-core-modified porphyrins",

abstract = "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 1H NMR results along with DFT calculations. This journal is",

author = "Chihiro Maeda and Motoki Masuda and Naoki Yoshioka",

year = "2014",

month = may,

day = "7",

doi = "10.1039/c3ob42564a",

language = "English",

volume = "12",

pages = "2656--2662",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "17",

}

TY - JOUR

T1 - Synthesis of carbazole-based hetero-core-modified porphyrins

AU - Maeda, Chihiro

AU - Masuda, Motoki

AU - Yoshioka, Naoki

PY - 2014/5/7

Y1 - 2014/5/7

N2 - 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 1H NMR results along with DFT calculations. This journal is

AB - 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 1H NMR results along with DFT calculations. This journal is

UR - http://www.scopus.com/inward/record.url?scp=84898066333&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84898066333&partnerID=8YFLogxK

U2 - 10.1039/c3ob42564a

DO - 10.1039/c3ob42564a

M3 - Article

AN - SCOPUS:84898066333

SN - 1477-0520

VL - 12

SP - 2656

EP - 2662

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 17

ER -

Synthesis of carbazole-based hetero-core-modified porphyrins

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this