Atropisomerism in a Belt-Persistent Nanohoop Molecule: Rotational Restriction Forced by Macrocyclic Ring Strain

被引:46
作者
Hitosugi, Shunpei [1 ]
Nakanishi, Waka [1 ]
Isobe, Hiroyuki [1 ]
机构
[1] Tohoku Univ, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
关键词
atropisomerism; biaryls; isomerization; macrocycles; nanotubes;
D O I
10.1002/asia.201200187
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enough strain! Strain in a macrocyclic ring hinders the rotation of an arylene panel in a nanohoop molecule containing four chrysenylene units (see picture). Unlike conventional rotational restrictions in biaryl systems, the new atropisomerism does not require any steric hinderance from the substituents. The study of atropisomerism also provides the first experimental insights into the relative stability of nanohoop structures. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1550 / 1552
页数:3
相关论文
共 25 条
[1]   The stereochemistry of diphenyls and analogous compounds [J].
Adams, R ;
Yuan, HC .
CHEMICAL REVIEWS, 1933, 12 (02) :261-338
[2]   DFT Study of [2.2]-, [3.3]-, and [4.4]Paracyclophanes: Strain Energy, Conformations, and Rotational Barriers [J].
Bachrach, Steven M. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2011, 115 (11) :2396-2401
[3]   A computational study of [2.2]cyclophanes [J].
Caramori, GF ;
Galembeck, SE ;
Laali, KK .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3242-3250
[4]   The molecular configurations of polynuclear aromatic compounds. Part I. The resolution of gamma-6 : 6'-dinitro- and 4 : 6 : 4': 6'-tetranitro-diphenic acids into optically active components. [J].
Christie, GH ;
Kenner, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1922, 121 :614-620
[5]  
Eliel E. L., 1994, STEREOCHEMISTRY ORGA
[6]   Iridium-catalyzed direct borylation of phenacenes [J].
Hitosugi, Shunpei ;
Nakamura, Yuta ;
Matsuno, Taisuke ;
Nakanishi, Waka ;
Isobe, Hiroyuki .
TETRAHEDRON LETTERS, 2012, 53 (09) :1180-1182
[7]   Bottom-up synthesis of finite models of helical (n,m)-single-wall carbon nanotubes [J].
Hitosugi, Shunpei ;
Nakanishi, Waka ;
Yamasaki, Takashi ;
Isobe, Hiroyuki .
NATURE COMMUNICATIONS, 2011, 2
[8]   Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cycloparaphenylene: Carbon Nanohoop Structures [J].
Jasti, Ramesh ;
Bhattacharjee, Joydeep ;
Neaton, Jeffrey B. ;
Bertozzi, Carolyn R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (52) :17646-+
[9]   Crystalline molecular machines:: A quest toward solid-state dynamics and function [J].
Khuong, Tinh-Alfredo V. ;
Nunez, Jose E. ;
Godinez, Carlos E. ;
Garcia-Garibay, Miguel A. .
ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (06) :413-422
[10]   Stereochemistry of Carbon Nanotubes [J].
Komatsu, Naoki .
JAPANESE JOURNAL OF APPLIED PHYSICS, 2010, 49 (02)