Polymethacrylic zinc porphyrin: A new approach to chiral recognition

被引:12
作者
Angiolini, Luigi
Benelli, Tiziana [1 ]
Giorgini, Loris
机构
[1] Univ Bologna, Dipartimento Chim Ind & Mat, I-40136 Bologna, Italy
关键词
Polymeric porphyrins; Chiral recognition; Circular dichroism; COUPLED CIRCULAR-DICHROISM; HOST-GUEST COMPLEXATION; ENANTIOSELECTIVE EPOXIDATION; ABSOLUTE-CONFIGURATIONS; ELECTRONIC-STRUCTURE; METALLOPORPHYRIN; TWEEZER; METAL; ABSORPTION; POLYMERS;
D O I
10.1016/j.reactfunctpolym.2010.12.005
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A methacrylic homopolymer bearing in the side-chain achiral zinc tetraarylporphyrin moieties, has been studied as macromolecular chromophoric host to determine the absolute configuration of alpha,omega-diamines. The polymeric material resulted able to bind the chiral guest through amine nitrogen/zinc coordination to form a complex which exhibits exciton-coupled bisignate circular dichroism (CD) spectra, due to stereodifferentiation leading to a preferred porphyrin helicity. The sign of CD signal reflects the absolute configuration of diamine and the method turns out very sensitive, requiring only few microgram quantities of guest compound. To our knowledge this is the first example of absolute configuration assignment to chiral molecular compounds by means of a polymeric derivative containing in the side-chain metallo-porphyrins moieties. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:204 / 209
页数:6
相关论文
共 44 条
[1]  
[Anonymous], 1978, The Porphyrins, DOI [10.1016/B978-0-12-220103-5.50008-8, DOI 10.1016/B978-0-12-220103-5.50008-8]
[2]   Sugar-controlled aggregate formation in boronic acid-appended porphyrin amphiphiles [J].
Arimori, S ;
Takeuchi, M ;
Shinkai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (01) :245-246
[3]  
Berova N., 2000, CIRCULAR DICHROISM P, V2nd, P337
[4]   Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts [J].
Berova, Nina ;
Pescitelli, Gennaro ;
Petrovic, Ana G. ;
Proni, Gloria .
CHEMICAL COMMUNICATIONS, 2009, (40) :5958-5980
[5]   Origin, control, and application of supramolecular chirogenesis in bisporphyrin-based systems [J].
Borovkov, VV ;
Hembury, GA ;
Inoue, Y .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (07) :449-459
[6]  
BUCHLER JW, 1978, PORPHYRINS, V1, P425
[7]   MICROSCALE STRUCTURE DETERMINATION OF OLIGOSACCHARIDES BY THE EXCITON CHIRALITY METHOD [J].
CHANG, M ;
MEYERS, HV ;
NAKANISHI, K ;
OJIKA, M ;
HILL, J ;
PARK, MH ;
TAKEDA, R ;
VAZQUEZ, JT ;
WIESLER, WT .
PURE AND APPLIED CHEMISTRY, 1989, 61 (07) :1193-1200
[8]   LONG-RANGE EFFECT IN EXCITON CHIRALITY METHOD [J].
CHEN, SML ;
HARADA, N ;
NAKANISHI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (23) :7352-7354
[9]   REGIOSELECTIVE AND ENANTIOSELECTIVE EPOXIDATION CATALYZED BY METALLOPORPHYRINS [J].
COLLMAN, JP ;
ZHANG, XM ;
LEE, VJ ;
UFFELMAN, ES ;
BRAUMAN, JI .
SCIENCE, 1993, 261 (5127) :1404-1411
[10]   INTERPRETATION OF PORPHYRIN AND METALLOPORPHYRIN SPECTRA [J].
CORWIN, AH ;
CHIVVIS, AB ;
POOR, RW ;
WHITTEN, DG ;
BAKER, EW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (24) :6577-&