Self-assembly, binding, and dynamic properties of heterodimeric porphyrin macrocycles

被引:41
作者
Ballester, P [1 ]
Costa, A
Deyà, PM
Frontera, A
Gomila, RM
Oliva, AI
Sanders, JKM
Hunter, CA
机构
[1] ICREA, Tarragona 43007, Spain
[2] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[3] Univ Illes Balears, Dept Quim, E-07071 Palma de Mallorca, Spain
[4] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
[5] Univ Sheffield, Dept Chem, Krebs Inst Biomol Sci, Ctr Chem Biol, Sheffield S3 7HF, S Yorkshire, England
关键词
D O I
10.1021/jo0505369
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A series of heterodimeric tetralactam macrocycles have been self-assembled using two kinetically labile zinc porphyrin-pyridine interactions. The stability constants have been determined by UVvis titrations in CHCl(3). The stability constants depend on the degree of preorganization of the linker units connecting the interacting groups. The ability of the self-assembled macrocycles to bind a terephthalamide guest was also investigated. One of the macrocycles was used for the construction of a [2]rotaxane. The dynamic properties of this system provide insight into the exchange mechanisms that operate in complex noncovalent assemblies.
引用
收藏
页码:6616 / 6622
页数:7
相关论文
共 25 条
[1]   TWO-DIMENSIONAL NMR EXCHANGE SPECTROSCOPY - QUANTITATIVE TREATMENT OF MULTISITE EXCHANGING SYSTEMS [J].
ABEL, EW ;
COSTON, TPJ ;
ORRELL, KG ;
SIK, V ;
STEPHENSON, D .
JOURNAL OF MAGNETIC RESONANCE, 1986, 70 (01) :34-53
[2]   LIGAND-BINDING BY BUTADIYNE-LINKED PORPHYRIA DIMERS, TRIMERS AND TETRAMERS [J].
ANDERSON, HL ;
ANDERSON, S ;
SANDERS, JKM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18) :2231-2245
[3]  
Balzani V, 2000, ANGEW CHEM INT EDIT, V39, P3348, DOI 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO
[4]  
2-X
[5]   Chiroptical switching in a bistable molecular shuttle [J].
Bottari, G ;
Leigh, DA ;
Pérez, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (44) :13360-13361
[6]   THE SYNTHESIS OF BIS-(DIALKYLAMINOALKYL) ESTERS OF 5-METHOXYISOPHTHALIC ACID [J].
CALANDRA, JC ;
SVARZ, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (02) :1027-1028
[7]   Efficient modulation of hydrogen-bonding interactions by remote substituents [J].
Chang, SY ;
Kim, HS ;
Chang, KJ ;
Jeong, KS .
ORGANIC LETTERS, 2004, 6 (02) :181-184
[8]   Self-assembly and binding properties of a metallomacrocycle having two interactive binding subcavities [J].
Chang, SY ;
Um, MC ;
Uh, H ;
Jang, HY ;
Jeong, KS .
CHEMICAL COMMUNICATIONS, 2003, (16) :2026-2027
[9]   SOME DERIVATIVES OF 4-AMINO-PYRIDINE AND 4-NITRO-PYRIDINE [J].
ESSERY, JM ;
SCHOFIELD, K .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (DEC) :4953-4959
[10]  
FOSDICK LS, 1941, J AM CHEM SOC, V63, P1277