Hydrogen bonding control of molecular self-assembly: Aggregation behavior of acylaminopyridine-carboxylic acid derivatives in solution and the solid state

被引:51
作者
Zafar, A
Geib, SJ
Hamuro, Y
Carr, AJ
Hamilton, AD
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
基金
美国国家科学基金会;
关键词
self-assembly; hydrogen bonding; acylaminopyridine-carboxylic acid;
D O I
10.1016/S0040-4020(00)00733-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this paper we report the design, synthesis and investigation of a family of acylaminopyridine-carboxylic acid monomers that can aggregate through bidentate hydrogen bonding interactions between the carboxylic acid and the aminopyridine sites. We show that in solution the nature of the aggregate depends on the substitution pattern of the monomer and present evidence from NMR and mass spectrometry that in some cases cyclic association occurs. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8419 / 8427
页数:9
相关论文
共 17 条
[1]   Cylindrical β-sheet peptide assemblies [J].
Clark, TD ;
Buriak, JM ;
Kobayashi, K ;
Isler, MP ;
McRee, DE ;
Ghadiri, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :8949-8962
[2]   Self-assembling capsules [J].
Conn, MM ;
Rebek, J .
CHEMICAL REVIEWS, 1997, 97 (05) :1647-1668
[3]   THE DESIGN OF MOLECULAR HOSTS, GUESTS, AND THEIR COMPLEXES (NOBEL LECTURE) [J].
CRAM, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (08) :1009-1020
[4]  
FREDERICKS JR, 1996, COMPREHENSIVE SUPRAM, V9, P565
[5]   MOLECULAR RECOGNITION IN THE SOLID-STATE - CONTROLLED ASSEMBLY OF HYDROGEN-BONDED MOLECULAR SHEETS [J].
GARCIATELLADO, F ;
GEIB, SJ ;
GOSWAMI, S ;
HAMILTON, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9265-9269
[6]   THE CRYSTAL STRUCTURE OF ACETIC ACID [J].
JONES, RE ;
TEMPLETON, DH .
ACTA CRYSTALLOGRAPHICA, 1958, 11 (07) :484-487
[7]   Self-assembly of rodlike hydrogen-bonded nanostructures [J].
Klok, HA ;
Jolliffe, KA ;
Schauer, CL ;
Prins, LJ ;
Spatz, JP ;
Möller, M ;
Timmerman, P ;
Reinhoudt, DN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) :7154-7155
[8]   Self-assembly mediated by the donor-donor-acceptor• acceptor-acceptor-donor (DDA•AAD) hydrogen-bonding motif:: Formation of a robust hexameric aggregate [J].
Kolotuchin, SV ;
Zimmerman, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9092-9093
[9]   SELF-ASSEMBLING SUPRAMOLECULAR COMPLEXES [J].
LAWRENCE, DS ;
JIANG, T ;
LEVETT, M .
CHEMICAL REVIEWS, 1995, 95 (06) :2229-2260
[10]   Self-complementary hydrogen bonding heterocycles designed for the enforced self-assembly into supramolecular macrocycles [J].
Marsh, A ;
Silvestri, M ;
Lehn, JM .
CHEMICAL COMMUNICATIONS, 1996, (13) :1527-1528