Chiral amplification of chiral porphyrin derivatives by templated heteroaggregation

被引:52
作者
Monti, Donato
Venanzi, Mariano
Stefanelli, Manuela
Sorrenti, Alessandro
Mancini, Giovanna
Di Natale, Corrado
Paolesse, Roberto
机构
[1] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, I-00133 Rome, Italy
[2] Univ Roma La Sapienza, IMC, CNR, Dipartimento Chim, I-00185 Rome, Italy
[3] Univ Roma Tor Vergata, Dipartimento Ingn Elettron, I-00133 Rome, Italy
关键词
D O I
10.1021/ja071249k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The solvent-promoted aggregation of amphiphilic porphyrin derivatives 1H(2) and 2H(2), possessing a chiral cationic or anionic functionality, respectively, occurs with the formation of chiral supramolecular structures. If the aggregation of 1H(2) (P*(+) in the artwork) is carried out in the presence of preformed aggregates of 2H(2) (P*(-) in the artwork), a remarkable amplification of the supramolecular chirality is observed (P*(+) + P*(-), in the picture) as a consequence of an electrostatic templation effect. The templated heteroaggregates resulted also in increased stability toward the presence of an achiral, negatively charged, porphyrin derivative.
引用
收藏
页码:6688 / +
页数:3
相关论文
共 27 条
[1]   Tailoring porphyrins and chlorins for self-assembly in biomimetic artificial antenna systems [J].
Balaban, TS .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (08) :612-623
[2]   A cationic zinc porphyrin as a chiroptical probe for Z-DNA [J].
Balaz, M ;
De Napoli, M ;
Holmes, AE ;
Mammana, A ;
Nakanishi, K ;
Berova, N ;
Purrello, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4006-4009
[3]   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
[4]   Solid-state supramolecular chirogenesis: High optical activity and gradual development of zinc octaethylporphyrin aggregates [J].
Borovkov, VV ;
Harada, T ;
Hembury, GA ;
Inoue, Y ;
Kuroda, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1746-1749
[5]   Interaction of a chirally functionalised porphyrin derivative with chiral micellar aggregates. Construction of a system with stereoselective cytochrome-P450 biomimetic activity [J].
Cantonetti, V ;
Monti, D ;
Venanzi, M ;
Bombelli, C ;
Ceccacci, F ;
Mancini, G .
TETRAHEDRON-ASYMMETRY, 2004, 15 (13) :1969-1977
[6]   Chirality amplification of porphyrin assemblies exclusively constructed from achiral porphyrin derivatives [J].
Chen, Penglei ;
Ma, Xiaoguang ;
Duan, Pengfei ;
Liu, Minghua .
CHEMPHYSCHEM, 2006, 7 (11) :2419-2423
[7]   Hierarchical porphyrin self-assembly in aqueous solution [J].
De Napoli, M ;
Nardis, S ;
Paolesse, R ;
Vicente, MGH ;
Lauceri, R ;
Purrello, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5934-5935
[8]   Effective cation-assisted chirality induction using a dibenzo-diaza-30-crown-10 with bis(zinc(II) porphyrin) units [J].
Kubo, Y ;
Ishii, Y ;
Yoshizawa, T ;
Tokita, S .
CHEMICAL COMMUNICATIONS, 2004, (12) :1394-1395
[9]   From achiral porphyrins to template-imprinted chiral aggregates and further. Self-replication of chiral memory from scratch [J].
Lauceri, R ;
Raudino, A ;
Scolaro, LM ;
Micali, N ;
Purrello, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :894-895
[10]   Supramolecular chirality control by solvent changes. Solvodichroic effect on chiral porphyrin aggregation [J].
Monti, D ;
Venanzi, M ;
Mancini, G ;
Di Natale, C ;
Paolesse, R .
CHEMICAL COMMUNICATIONS, 2005, (19) :2471-2473