Bending contorted hexabenzocoronene into a bowl

被引:65
作者
Whalley, Adam C. [1 ]
Plunkett, Kyle N. [2 ]
Gorodetsky, Alon A. [1 ]
Schenck, Christine L. [1 ]
Chiu, Chien-Yang [1 ]
Steigerwald, Michael L. [1 ]
Nuckolls, Colin [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
[2] So Illinois Univ, Dept Chem, Carbondale, IL 62901 USA
基金
美国国家科学基金会;
关键词
BUCKYCATCHER; HYDROCARBON; MOLECULES; SUMANENE; C-70; C-60;
D O I
10.1039/c0sc00470g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This article describes the synthesis of a new type of bowl-shaped polycyclic aromatic hydrocarbon. These bowls are formed by joining the proximal carbons of contorted hexabenzocoronenes. These methods begin to tap a wealth of structural diversity available from these core structures. The bowl-shaped hydrocarbons more easily accept electrons than their contorted hexabenzocoronene precursors and associate strongly with C-70.
引用
收藏
页码:132 / 135
页数:4
相关论文
共 23 条
[1]   Synthesis of Highly Strained π-Bowls from Sumanene [J].
Amaya, Toru ;
Nakata, Takuto ;
Hirao, Toshikazu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10810-+
[2]   MNDO STUDY OF LARGE CARBON CLUSTERS [J].
BAKOWIES, D ;
THIEL, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3704-3714
[3]   Enforced one-dimensional photoconductivity in core-cladding hexabenzocoronenes [J].
Cohen, Yaron S. ;
Xiao, Shengxiong ;
Steigerwald, Michael L. ;
Nuckolls, Colin ;
Kagan, Cherie R. .
NANO LETTERS, 2006, 6 (12) :2838-2841
[4]   One step Pd(0)-catalyzed synthesis, X-ray analysis, and photophysical properties of cyclopent[hi]aceanthrylene:: Fullerene-like properties in a nonalternant cyclopentafused aromatic hydrocarbon [J].
Dang, H ;
Levitus, M ;
Garcia-Garibay, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (01) :136-143
[5]   C3v-Symmetrical Tribenzotriquinacenes as Hosts for C60 and C70 in Solution and in the Solid State [J].
Georghiou, Paris E. ;
Dawe, Louise N. ;
Tran, Huu-Anh ;
Struebe, Joerg ;
Neumann, Beate ;
Stammler, Hans-Georg ;
Kuck, Dietmar .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :9040-9047
[6]   PI-ORBITAL CONJUGATION AND REHYBRIDIZATION IN BRIDGED ANNULENES AND DEFORMED MOLECULES IN GENERAL - PI-ORBITAL AXIS VECTOR ANALYSIS [J].
HADDON, RC ;
SCOTT, LT .
PURE AND APPLIED CHEMISTRY, 1986, 58 (01) :137-142
[8]   THE STRUCTURE OF OVERCROWDED AROMATIC COMPOUNDS .3. THE CRYSTAL STRUCTURE OF 3-4-BENZOPHENANTHRENE [J].
HERBSTEIN, FH ;
SCHMIDT, GMJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (OCT) :3302-3313
[9]   Self-Association and Electron Transfer in Donor-Acceptor Dyads Connected by meta-Substituted Oligomers [J].
Molina-Ontoria, Agustin ;
Fernandez, Gustavo ;
Wielopolski, Mateusz ;
Atienza, Carmen ;
Sanchez, Luis ;
Gouloumis, Andreas ;
Clark, Timothy ;
Martin, Nazario ;
Guldi, Dirk M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) :12218-12229
[10]   Inclusion complexes of buckycatcher with C60 and C70 [J].
Mueck-Lichtenfeld, Christian ;
Grimme, Stefan ;
Kobryn, Lesya ;
Sygula, Andrzej .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2010, 12 (26) :7091-7097