A Twisted Nanographene Consisting of 96 Carbon Atoms

被引：84

作者：

Cheung, Kwan Yin ^{[1
]}

Chan, Chi Kit ^{[1
]}

Liu, Zhifeng ^{[1
]}

Miao, Qian ^{[1
]}

机构：

[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 31期

关键词：

arenes; aromaticity; polycycles; stereochemistry; strained molecules; POLYCYCLIC AROMATIC-HYDROCARBON; AGGREGATION-INDUCED EMISSION; STRUCTURAL-ANALYSIS; GRAPHITIC CARBON; SCHOLL REACTION; HEXABENZOCORONENE; TWISTACENE; CHEMISTRY; EFFICIENT; SADDLES;

D O I：

10.1002/anie.201703754

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we report synthesis, structure and properties of a new type of twisted nanographene, which contains an [8]circulene moiety in a polycyclic framework of 96 sp(2) carbon atoms. The key steps in this synthesis are the Diels-Alder reaction of a macrocyclic diyne and the subsequent Scholl reaction forming the [8]circulene moiety. Two incompletely cyclized products were isolated from the Scholl reaction, providing insight into the cyclization of the strained octagon. This nanographene is twisted along two directions with end-to-end twists of 142.4 degrees and 140.2 degrees as revealed by X-ray crystallography, and is flexible at room temperature as found from the computational and experimental studies.

引用

页码：9003 / 9007

页数：5

共 53 条

[31] Synthesis and Structural Data of Tetrabenzo[8] circulene [J].

Miller, Robert W. ;

Duncan, Alexandra K. ;

Schneebeli, Severin T. ;

Gray, Danielle L. ;

Whalley, Adam C. .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (13) :3705-3711

[32] Twisted pyrene-fused azaacenes [J].

More, Sandeep ;

Choudhary, Sunil ;

Higelin, Alexander ;

Krossing, Ingo ;

Melle-Franco, Manuel ;

Mateo-Alonso, Aurelio .

CHEMICAL COMMUNICATIONS, 2014, 50 (16) :1976-1979

[33] New advances in nanographene chemistry [J].

Narita, Akimitsu ;

Wang, Xiao-Ye ;

Feng, Xinliang ;

Muellen, Klaus .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (18) :6616-6643

[34] Electric field effect in atomically thin carbon films [J].

Novoselov, KS ;

Geim, AK ;

Morozov, SV ;

Jiang, D ;

Zhang, Y ;

Dubonos, SV ;

Grigorieva, IV ;

Firsov, AA .

SCIENCE, 2004, 306 (5696) :666-669

[35] Negatively curved carbon as the anode for lithium ion batteries [J].

Odkhuu, Dorj ;

Jung, Dong Hyun ;

Lee, Hosik ;

Han, Sang Soo ;

Choi, Seung-Hoon ;

Ruoff, Rodney S. ;

Park, Noejung .

CARBON, 2014, 66 :39-47

[36] Magnetism in all-carbon nanostructures with negative gaussian curvature -: art. no. 237204 [J].

Park, N ;

Yoon, M ;

Berber, S ;

Ihm, J ;

Osawa, E ;

Tománek, D .

PHYSICAL REVIEW LETTERS, 2003, 91 (23)

[37] Designing rigid carbon foams [J].

Park, Sora ;

Kittimanapun, Kritsada ;

Ahn, Jeung Sun ;

Kwon, Young-Kyun ;

Tomanek, David .

JOURNAL OF PHYSICS-CONDENSED MATTER, 2010, 22 (33)

[38]

Qiao X., 1997, ANGEW CHEM, V109, P1588

[39] An extraordinarily twisted polycyclic aromatic hydrocarbon [J].

Qiao, XX ;

Ho, DM ;

Pascal, RA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1531-1532

[40] Chirality in curved polyaromatic systems [J].

Rickhaus, Michel ;

Mayor, Marcel ;

Juricek, Michal .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (06) :1643-1660

← 1 2 3 4 5 6 →