Hydrogen bonded dimers of triurea derivatives of triphenylmethanes

被引:33
作者
Rudzevich, Y
Rudzevich, V
Schollmeyer, D
Thondorf, I
Bohmer, V
机构
[1] Univ Mainz, Abt Lehramt Chem, Fachbereich Chem & Pharm, D-55099 Mainz, Germany
[2] Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany
[3] Univ Halle Wittenberg, Inst Biochem, Fachbereich Biochem Biotechnol, D-06099 Halle Saale, Germany
关键词
D O I
10.1021/ol0476265
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tri-(2-alkoxy-5-ureido-phenyl)methanes represent a novel self-complementary motif forming hydrogen bonded homo- and heterodimers in nonpolar, aprotic solvents as evidenced by H-1 NMR and ESI-mass spectra and by the formation of heterodimers. MD simulations suggest the formation of hydrogen bonds of different strength in agreement with NMR data. The dimerization does not interfere with that of tetraurea calix[4]arenes. A combination of both motifs may be used therefore to build up larger structures via self-assembly processes.
引用
收藏
页码:613 / 616
页数:4
相关论文
共 30 条
[11]   A CONVENIENT AND GENERAL-SYNTHESIS OF ALKANEDIYL DIPHENOLS [J].
GRUTTNER, C ;
BOHMER, V ;
ASSMUS, R ;
SCHERF, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (02) :93-94
[12]   TRIPHENYLCARBINOL DERIVATIVES AS MOLECULES FOR 2ND-ORDER NONLINEAR OPTICS [J].
KELDERMAN, E ;
STARMANS, WAJ ;
VANDUYNHOVEN, JPM ;
VERBOOM, W ;
ENGBERSEN, JFJ ;
REINHOUDT, DN ;
DERHAEG, L ;
VERBIEST, T ;
CLAYS, K ;
PERSOONS, A .
CHEMISTRY OF MATERIALS, 1994, 6 (04) :412-417
[13]   N,N′-disubstituted ureas:: Influence of substituents on the formation of supramolecular polymers [J].
Lortie, F ;
Boileau, S ;
Bouteiller, L .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (13) :3008-3014
[14]   Hydrogen-bonded dimers of tetraurea calix[4]arenes: Unambiguous proof by single crystal X-ray analysis [J].
Mogck, O ;
Paulus, EF ;
Bohmer, V ;
Thondorf, I ;
Vogt, W .
CHEMICAL COMMUNICATIONS, 1996, (22) :2533-2534
[15]   Social self-sorting in aqueous solution [J].
Mukhopadhyay, P ;
Wu, AX ;
Isaacs, L .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19) :6157-6164
[16]  
Prins LJ, 2002, CHEM-EUR J, V8, P2302, DOI 10.1002/1521-3765(20020517)8:10<2302::AID-CHEM2302>3.0.CO
[17]  
2-C
[18]   Kinetic stabilities of double, tetra-, and hexarosette hydrogen-bonded assemblies [J].
Prins, LJ ;
Neuteboom, EE ;
Paraschiv, V ;
Crego-Calama, M ;
Timmerman, P ;
Reinhoudt, DN .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4808-4820
[19]  
Prins LJ, 2002, CHEM-EUR J, V8, P2288, DOI 10.1002/1521-3765(20020517)8:10<2288::AID-CHEM2288>3.0.CO
[20]  
2-3