Further insight into aryl nitration of tetraphenylporphyrin

被引：11

作者：

Xue, Zhi ^{[2
]}

Lee, Priscilla P. S. ^{[2
]}

Wang, Yanming ^{[2
]}

Kwong, Daniel W. J. ^{[1
]}

Li, Jing ^{[2
]}

Xin, John H. ^{[2
]}

Wong, Wai-Kwok ^{[1
]}

Cheuk, Kevin K. L. ^{[2
]}

机构：

[1] Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R China

[2] Hong Kong Polytech Univ, Nanotechnol Ctr, Inst Text & Clothing, Hunghom, Hong Kong, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 33期

关键词：

Porphyrin synthesis; Porphyrin functionalization; Tetra-meso-phenylporphyrin; Nitration; 5,10,15,20-Tetrakis(4-nitrophenyl)-21H,23H-porphyrin; PORPHYRIN DEGRADATION; HEME-OXYGENASE; TETRAARYLPORPHYRINS; COORDINATION; CHEMISTRY; NETWORKS;

D O I：

10.1016/j.tet.2011.06.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p-nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6030 / 6035

页数：6

共 42 条

[1]

Armstrong NR, 2000, J PORPHYR PHTHALOCYA, V4, P414, DOI 10.1002/(SICI)1099-1409(200006/07)4:4<414::AID-JPP247>3.3.CO

[2]

2-2

[3] CONTROL OF REACTIVITY AT THE PORPHYRIN PERIPHERY BY METAL-ION COORDINATION - A GENERAL-METHOD FOR SPECIFIC NITRATION AT THE BETA-PYRROLIC POSITION OF 5,10,15,20-TETRA-ARYLPORPHYRINS [J].

CATALANO, MM ;

CROSSLEY, MJ ;

HARDING, MM ;

KING, LG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (22) :1535-1536

[4]

Di Natale Corrado, 2010, Materials Today, V13, P46, DOI 10.1016/S1369-7021(10)70127-9

[5] Self-Organized Porphyrinic Materials [J].

Drain, Charles Michael ;

Varotto, Alessandro ;

Radivojevic, Ivana .

CHEMICAL REVIEWS, 2009, 109 (05) :1630-1658

[6] Diastereochemically controlled porphyrin dimer formation on a DNA duplex scaffold [J].

Endo, Masayuki ;

Fujitsuka, Mamoru ;

Majima, Tetsuro .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (03) :1106-1112

[7] SUBSTITUENT EFFECTS ON VALENCE IONIZATION-POTENTIALS OF FREE-BASE PORPHYRINS - LOCAL-DENSITY FUNCTIONAL CALCULATIONS AND THEIR RELEVANCE TO ELECTROCHEMICAL AND PHOTOELECTRON SPECTROSCOPIC STUDIES [J].

GHOSH, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) :4691-4699

[8] NOVEL SYNTHESIS OF 5,10,15,20-TETRAARYLPORPHYRINS USING HIGH-VALENT TRANSITION-METAL SALTS [J].

GRADILLAS, A ;

DELCAMPO, C ;

SINISTERRA, JV ;

LLAMA, EF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (20) :2611-2613

[9] Titrations in non-aqueous media:: potentiometric investigation of symmetrical and unsymmetrical tetra-aryl porphyrins with 4-nitrophenyl and 4-aminophenyl substituents in nitrobenzene solvent [J].

Gündüz, N ;

Gündüz, T ;

Hayvali, M .

TALANTA, 1999, 48 (01) :71-79

[10] Hyperbranched porphyrins -: a rapid synthetic approach to multiporphyrin macromolecules [J].

Hecht, S ;

Emrick, T ;

Fréchet, JMJ .

CHEMICAL COMMUNICATIONS, 2000, (04) :313-314

← 1 2 3 4 5 →