Direct and Regioselective Amination of β-Unsubstituted 5,15-Diazaporphyrins with Amines: A Convenient Route to Near-Infrared-Responsive Diazaporphyrin Sensitizers

Satoshi Omomo, Takuma Sugai, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

We have established a convenient method for the base-promoted direct amination of β-unsubstituted 5,15-diazaporphyrins (DAPs) with secondary and primary amines to produce 3,7,13,17-tetraamino- and 3-amino-DAPs, respectively, regioselectively. The amino groups attached at the periphery cause significant red shifts of the absorption bands as a result of their perturbation of the HOMO and/or LUMO in the DAP π-system. The palladium complex of a 3,7,13,17-tetrakis(diphenylamino)-DAP generated singlet oxygen in high yield under irradiation with near-infrared light.

Original languageEnglish
Pages (from-to)3797-3800
Number of pages4
JournalAngewandte Chemie - International Edition
Volume57
Issue number14
DOIs
Publication statusPublished - Mar 26 2018

Fingerprint

Amination
Singlet Oxygen
Palladium
Amines
Absorption spectra
Irradiation
Infrared radiation
Oxygen

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Direct and Regioselective Amination of β-Unsubstituted 5,15-Diazaporphyrins with Amines : A Convenient Route to Near-Infrared-Responsive Diazaporphyrin Sensitizers. / Omomo, Satoshi; Sugai, Takuma; Minoura, Mao; Nakano, Haruyuki; Matano, Yoshihiro.

In: Angewandte Chemie - International Edition, Vol. 57, No. 14, 26.03.2018, p. 3797-3800.

Research output: Contribution to journalArticle

@article{91ff65a2c15b47ce9bf3307e961d74e0,
title = "Direct and Regioselective Amination of β-Unsubstituted 5,15-Diazaporphyrins with Amines: A Convenient Route to Near-Infrared-Responsive Diazaporphyrin Sensitizers",
abstract = "We have established a convenient method for the base-promoted direct amination of β-unsubstituted 5,15-diazaporphyrins (DAPs) with secondary and primary amines to produce 3,7,13,17-tetraamino- and 3-amino-DAPs, respectively, regioselectively. The amino groups attached at the periphery cause significant red shifts of the absorption bands as a result of their perturbation of the HOMO and/or LUMO in the DAP π-system. The palladium complex of a 3,7,13,17-tetrakis(diphenylamino)-DAP generated singlet oxygen in high yield under irradiation with near-infrared light.",
author = "Satoshi Omomo and Takuma Sugai and Mao Minoura and Haruyuki Nakano and Yoshihiro Matano",
year = "2018",
month = "3",
day = "26",
doi = "10.1002/anie.201800471",
language = "English",
volume = "57",
pages = "3797--3800",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "14",

}

TY - JOUR

T1 - Direct and Regioselective Amination of β-Unsubstituted 5,15-Diazaporphyrins with Amines

T2 - A Convenient Route to Near-Infrared-Responsive Diazaporphyrin Sensitizers

AU - Omomo, Satoshi

AU - Sugai, Takuma

AU - Minoura, Mao

AU - Nakano, Haruyuki

AU - Matano, Yoshihiro

PY - 2018/3/26

Y1 - 2018/3/26

N2 - We have established a convenient method for the base-promoted direct amination of β-unsubstituted 5,15-diazaporphyrins (DAPs) with secondary and primary amines to produce 3,7,13,17-tetraamino- and 3-amino-DAPs, respectively, regioselectively. The amino groups attached at the periphery cause significant red shifts of the absorption bands as a result of their perturbation of the HOMO and/or LUMO in the DAP π-system. The palladium complex of a 3,7,13,17-tetrakis(diphenylamino)-DAP generated singlet oxygen in high yield under irradiation with near-infrared light.

AB - We have established a convenient method for the base-promoted direct amination of β-unsubstituted 5,15-diazaporphyrins (DAPs) with secondary and primary amines to produce 3,7,13,17-tetraamino- and 3-amino-DAPs, respectively, regioselectively. The amino groups attached at the periphery cause significant red shifts of the absorption bands as a result of their perturbation of the HOMO and/or LUMO in the DAP π-system. The palladium complex of a 3,7,13,17-tetrakis(diphenylamino)-DAP generated singlet oxygen in high yield under irradiation with near-infrared light.

UR - http://www.scopus.com/inward/record.url?scp=85042592480&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85042592480&partnerID=8YFLogxK

U2 - 10.1002/anie.201800471

DO - 10.1002/anie.201800471

M3 - Article

C2 - 29396907

AN - SCOPUS:85042592480

VL - 57

SP - 3797

EP - 3800

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 14

ER -