A selectivity-driven supramolecular polymerization of an AB monomer

被引:114
作者
Scherman, OA [1 ]
Ligthart, GBWL [1 ]
Sijbesma, RP [1 ]
Meijer, EW [1 ]
机构
[1] Eindhoven Univ Technol, Lab Macromol & Organ Chem, NL-5600 MB Eindhoven, Netherlands
关键词
directionality; hydrogen bonds; metathesis; ring-opening polymerization; supramolecular polymers;
D O I
10.1002/anie.200504192
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Two become one: An AB-type monomer containing both 2-ureido-4[1H]-pyrimidinone and 2,7-diamido-1,8-naphthyridine quadruple hydrogen-bonding moieties is obtained by selective olefin cross metathesis. This monomer addresses the issue of stoichiometric imbalance in the self-assembly of AA + BB-type supramolecular polymers. Moreover, as the linker between both motifs is quite flexible, this monomer exists as a monocycle at low concentrations. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2072 / 2076
页数:5
相关论文
共 28 条
[1]   Cross-metathesis assisted by microwave irradiation [J].
Bargiggia, FC ;
Murray, WV .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9636-9639
[2]   Supramolecular polymers [J].
Brunsveld, L ;
Folmer, BJB ;
Meijer, EW ;
Sijbesma, RP .
CHEMICAL REVIEWS, 2001, 101 (12) :4071-4097
[3]   Supramolecular daisy chains [J].
Cantrill, SJ ;
Youn, GJ ;
Stoddart, JF ;
Williams, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :6857-6872
[4]   Polymerization [J].
Carothers, WH .
CHEMICAL REVIEWS, 1931, 8 (03) :353-426
[5]   Formation of discrete, functional assemblies and informational polymers through the hydrogen-bonding preferences of calixarene aryl and sulfonyl tetraureas [J].
Castellano, RK ;
Rebek, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3657-3663
[6]   Olefin metathesis involving ruthenium enoic carbene complexes [J].
Choi, TL ;
Lee, CW ;
Chatterjee, AK ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) :10417-10418
[7]  
Ciferri A., 2005, SUPRAMOLECULAR POLYM, V2nd
[8]   A microreactor for microwave-assisted capillary (continuous flow) organic synthesis [J].
Comer, E ;
Organ, MG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8160-8167
[9]   Self-association without regard to prototropy. A heterocycle that forms extremely stable quadruply hydrogen-bonded dimers [J].
Corbin, PS ;
Zimmerman, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) :9710-9711
[10]   MACROCYCLIZATION UNDER THERMODYNAMIC CONTROL - A THEORETICAL-STUDY AND ITS APPLICATION TO THE EQUILIBRIUM CYCLOOLIGOMERIZATION OF BETA-PROPIOLACTONE [J].
ERCOLANI, G ;
MANDOLINI, L ;
MENCARELLI, P ;
ROELENS, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3901-3908