Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cycloparaphenylene: Carbon Nanohoop Structures

被引:773
作者
Jasti, Ramesh [1 ,3 ]
Bhattacharjee, Joydeep [3 ]
Neaton, Jeffrey B. [3 ]
Bertozzi, Carolyn R. [1 ,2 ,3 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Howard Hughes Med Inst, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Dept Mol & Cell Biol, Howard Hughes Med Inst, Berkeley, CA 94720 USA
[3] Univ Calif Berkeley, Lawrence Berkeley Lab, Berkeley, CA 94720 USA
基金
美国国家科学基金会;
关键词
D O I
10.1021/ja807126u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first synthesis and characterization of [9]-, (12]-, and [18]cycloparaphenylene was demonstrated utilizing a novel aromatization reaction. We refer to these fascinating structures as "carbon nanohoops" due to their structural similarity to carbon nanotubes. Additionally, we have utilized computational methods to understand the unique properties of these fully conjugated macrocycles.
引用
收藏
页码:17646 / +
页数:3
相关论文
共 21 条
[1]   REACTIVITY OF 3,6-DIMETHOXY-3,6-DIMETHYLCYCLOHEXA-1,4-DIENE .2. REGIOSELECTIVE ARYLATION OF ELECTRON-RICH AROMATIC-COMPOUNDS [J].
ALONSO, F ;
YUS, M .
TETRAHEDRON, 1991, 47 (02) :313-316
[2]   REACTIVITY OF 3,6-DIMETHOXY-3,6-DIMETHYLCYCLOHEXA-1,4-DIENE .3. REGIOSELECTIVE ALPHA-ARYLATION OF KETONES VIA THEIR SILYL ENOL ETHERS [J].
ALONSO, F ;
YUS, M .
TETRAHEDRON, 1991, 47 (43) :9119-9124
[3]   EASY SYNTHESIS OF 2,4-DIALKYL SUBSTITUTED PHENOLS AND ANISOLES FROM PARA-BENZOQUINONE [J].
ALONSO, F ;
YUS, M .
TETRAHEDRON, 1992, 48 (13) :2709-2714
[4]   STEREOSELECTIVE 2-STEP CHEMICAL PREPARATION OF 1,4-DIALKYL-1,4-DIMETHOXYCYCLOHEXA-2,5-DIENES [J].
ALONSO, F ;
YUS, M .
TETRAHEDRON, 1991, 47 (35) :7471-7476
[5]   Carbon nanotubes: Synthesis, integration, and properties [J].
Dai, HJ .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (12) :1035-1044
[6]   THE STRUCTURE-DIRECTED SYNTHESIS OF CYCLACENE AND POLYACENE DERIVATIVES [J].
GIRRESER, U ;
GIUFFRIDA, D ;
KOHNKE, FH ;
MATHIAS, JP ;
PHILP, D ;
STODDART, JF .
PURE AND APPLIED CHEMISTRY, 1993, 65 (01) :119-125
[7]   The interplay of angle strain and aromaticity:: Molecular and electronic structures of [0n]paracyclophanes [J].
Jagadeesh, MN ;
Makur, A ;
Chandrasekhar, J .
JOURNAL OF MOLECULAR MODELING, 2000, 6 (02) :226-233
[8]   Ring-expanding metathesis of tetradehydroanthracene - Synthesis and structure of a tubelike, fully conjugated hydrocarbon [J].
Kammermeier, S ;
Jones, PG ;
Herges, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (22) :2669-2671
[9]   Ball-, bowl-, and belt-shaped conjugated systems and their complexing abilities:: Exploration of the concave-convex π-π interaction [J].
Kawase, Takeshi ;
Kurata, Hiroyuki .
CHEMICAL REVIEWS, 2006, 106 (12) :5250-5273
[10]   Reductive cleavage of benzyl ethers with lithium naphthalenide. A convenient method for debenzylation [J].
Liu, HJ ;
Yip, J ;
Shia, KS .
TETRAHEDRON LETTERS, 1997, 38 (13) :2253-2256