Social and antisocial [3+3] Schiff base macrocycles with isomeric backbones

被引:27
作者
Boden, Britta N. [1 ]
Hui, Joseph K. -H. [1 ]
MacLachlan, Mark J. [1 ]
机构
[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1021/jo801069g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two new conjugated macrocycles have been prepared in high yield using Schiff base condensation. These are the first Schiff base macrocycles to incorporate phenanthrene, and they contain 66 and 78 atoms, respectively, in their smallest closed ring. Although the backbones of the two macrocycles have nearly the same constitution, one aggregates in chloroform while the other does not. This is rationalized based on the differential overlap of aromatic components in the dimers.
引用
收藏
页码:8069 / 8072
页数:4
相关论文
共 52 条
[1]   Synthesis and crystal structure of a novel triangular macrocyclic molecule, tris(H2saloph), and its water complex [J].
Akine, S ;
Taniguchi, T ;
Nabeshima, T .
TETRAHEDRON LETTERS, 2001, 42 (50) :8861-8864
[2]   Core/shell oligometallic template synthesis of macrocyclic hexaoxime [J].
Akine, Shigehisa ;
Sunaga, Shuichi ;
Taniguchi, Takanori ;
Miyazaki, Hayato ;
Nabeshima, Tatsuya .
INORGANIC CHEMISTRY, 2007, 46 (08) :2959-2961
[3]   Tetraalkoxyphenanthrene: A new precursor for luminescent conjugated polymers [J].
Boden, BN ;
Jardine, KJ ;
Leung, ACW ;
MacLachlan, MJ .
ORGANIC LETTERS, 2006, 8 (09) :1855-1858
[4]   New diformyldihydroxyaromatic precursors for luminescent Schiff base macrocycles: Synthesis, characterization, and condensation studies [J].
Boden, Britta N. ;
Abdolmaleki, Amir ;
Ma, Cecily T. -Z. ;
MacLachlan, Mark J. .
CANADIAN JOURNAL OF CHEMISTRY, 2008, 86 (01) :50-64
[5]   Metal-free methods in the synthesis of macrocyclic Schiff bases [J].
Borisova, Nataliya E. ;
Reshetova, Marina D. ;
Ustynyuk, Yuri A. .
CHEMICAL REVIEWS, 2007, 107 (01) :46-79
[6]  
Cammidge AN., 1998, Handbook of liquid crystals, P693, DOI DOI 10.1002/9783527620623.CH4
[7]   Coordination-driven self-assembly: Solids with bidirectional porosity [J].
Campbell, K ;
Kuehl, CJ ;
Ferguson, MJ ;
Stang, PJ ;
Tykwinski, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7266-7267
[8]   Substituent effects on aromatic stacking interactions [J].
Cockroft, Scott L. ;
Perkins, Julie ;
Zonta, Cristiano ;
Adams, Harry ;
Spey, Sharon E. ;
Low, Caroline M. R. ;
Vinter, Jeremy G. ;
Lawson, Kevin R. ;
Urch, Christopher J. ;
Hunter, Christopher A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (07) :1062-1080
[9]   Tricopper(II) complexes of unsymmetrical macrocycles incorporating phenol and pyridine moieties: the development of two stepwise routes [J].
Croucher, Paul D. ;
Klingele, Marco H. ;
Noble, Andy ;
Brooker, Sally .
DALTON TRANSACTIONS, 2007, (36) :4000-4007
[10]   Shape-persistent macrocycles with intraannular polar groups:: Synthesis, liquid crystallinity, and 2D organization [J].
Fischer, M ;
Lieser, G ;
Rapp, A ;
Schnell, I ;
Mamdouh, W ;
De Feyter, S ;
De Schryver, FC ;
Höger, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) :214-222