Isolation of phlorin-dipyrrin conjugates from the acid-catalyzed condensation of dipyrromethanes and aldehydes

被引：18

作者：

Gryko, DT ^{[1
]}

Koszarna, B ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 15期

关键词：

porphyrinoids; oxidation; nitrogen heterocycles; aromatic substitution; phlorins;

D O I：

10.1002/ejoc.200500089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The product distribution of the acid-mediated condensation of dipyrromethanes and aldehydes was studied and a novel type of macrocycle phlorin-dipyrrin conjugate was isolated and identified by X-ray analysis. The generality of its formation from sterically hindered dipyrromethanes and pentafluorophenyldipyrromethane was demonstrated. The influence of the meso-aryl groups on the stability of the phlorin was studied. The reported two-step synthesis of a phlorin derivative is one of the simplest routes leading to this type of molecules. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

引用

页码：3314 / 3318

页数：5

共 45 条

[1]

Barbour L.J., 2001, J SUPRAMOL CHEM, V1, P189

[2] Synthesis of meso-phenyl-4,6-dipyrrins, preparation of their Cu(II), Ni(II), and Zn(II) chelates, and structural characterization of bis[meso-phenyl-4,6-dipyrrinato]Ni(II) [J].

Bruckner, C ;

Karunaratne, V ;

Rettig, SJ ;

Dolphin, D .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (11) :2182-2193

[3] Novel synthesis of hybrid calixphyrin macrocycles [J].

Bucher, C ;

Seidel, D ;

Lynch, V ;

Král, V ;

Sessler, JL .

ORGANIC LETTERS, 2000, 2 (20) :3103-3106

[4]

Fischer H, 1926, LIEBIGS ANN CHEM, V448, P178

[5]

FISHER H, 1924, BER DTSCH CHEM GES, V57, P610

[6] Confusion, inversion, and creation - a new spring from porphyrin chemistry [J].

Furuta, H ;

Maeda, H ;

Osuka, A .

CHEMICAL COMMUNICATIONS, 2002, (17) :1795-1804

[7] Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe [J].

Gabe, Y ;

Urano, Y ;

Kikuchi, K ;

Kojima, H ;

Nagano, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3357-3367

[8] Investigation of porphyrin-forming reactions.: Part 1.: Pyrrole plus aldehyde oligomerization in two-step, one-flask syntheses of meso-substituted porphyrins [J].

Geier, GR ;

Lindsey, JS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (05) :677-686

[9] A perspective of one-pot pyrrole-aldehyde condensations as versatile self-assembly processes [J].

Ghosh, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (15) :1918-1931

[10] Solvent-free condensation of pyrrole and pentafluorobenzaldehyde:: A novel synthetic pathway to corrole and oligopyrromethenes [J].

Gross, Z ;

Galili, N ;

Simkhovich, L ;

Saltsman, I ;

Botoshansky, M ;

Bläser, D ;

Boese, R ;

Goldberg, I .

ORGANIC LETTERS, 1999, 1 (04) :599-602

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