Hetero-double-helix formation by an ethynylhelicene oligomer possessing perfluorooctyl side chains

被引：54

作者：

Amemiya, Ryo ^{[1
]}

Saito, Nozomi ^{[1
]}

Yamaguchi, Masahiko ^{[1
]}

机构：

[1] Tohoku Univ, Dept Organ Chem, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 18期

关键词：

D O I：

10.1021/jo8010057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Monomeric to pentameric (P)-ethynylhelicene oligomers possessing perfluorooctyl side chains were synthesized. The circular dichroism (CD) and vapor pressure osomometry (VPO) studies indicated the formation of a helix-dimer for the (P)-pentamer, for example, in trifluoromethylbenzene at 5 degrees C at concentrations above 2 x 10(-6) M. Compared with a (P)-pentamer possessing decyloxycarbonyl side chains, the perfluorooctyl (P)-pentamer exhibited lower solubilities in organic solvents, formed a thermodynamically more stable helix-dimer, and exhibited a mirror image CD spectrum. The perfluorooctyl (P)-pentamer formed a hetero-helix dinner with a decyloxycarbonyl (M)-pentamer but not with a (P)-pentamer. It indicated higher stability of the hetero-helix dimer over the homo-helix dimers.

引用

页码：7137 / 7144

页数：8

共 47 条

[1]

Albecht M., 2005, ANGEW CHEM INT EDIT, V44, P6448

[2] Synthesis and structure of built-up organic macromolecules containing helicene [J].

Amemiya, Ryo ;

Yamaguchi, Masahiko .

CHEMICAL RECORD, 2008, 8 (02) :116-127

[3] Chiral recognition in noncovalent bonding interactions between helicenes: right-handed helix favors right-handed helix over left-handed helix [J].

Amemiya, Ryo ;

Yamaguchi, Masahiko .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (01) :26-35

[4] Dynamic chemical devices: Generation of reversible extension/contraction molecular motion by ion-triggered single/double helix interconversion [J].

Barboiu, M ;

Vaughan, G ;

Kyritsakas, N ;

Lehn, JM .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (03) :763-769

[5]

Berl V, 2001, CHEM-EUR J, V7, P2810, DOI 10.1002/1521-3765(20010702)7:13<2810::AID-CHEM2810>3.0.CO

[6]

2-5

[7] Interconversion of single and double helices formed from synthetic molecular strands [J].

Berl, V ;

Huc, I ;

Khoury, RG ;

Krische, MJ ;

Lehn, JM .

NATURE, 2000, 407 (6805) :720-723

[8]

Cheon KS, 2000, ANGEW CHEM INT EDIT, V39, P1482, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1482::AID-ANIE1482>3.0.CO

[9]

2-7

[10] Chiral architectures from macromolecular building blocks [J].

Cornelissen, JJLM ;

Rowan, AE ;

Nolte, RJM ;

Sommerdijk, NAJM .

CHEMICAL REVIEWS, 2001, 101 (12) :4039-4070

← 1 2 3 4 5 →