Synthesis of distorted nanographenes containing seven- and eight-membered carbocycles

被引:155
作者
Marquez, Irene R. [1 ]
Castro-Fernandez, Silvia [1 ]
Millan, Alba [1 ]
Campana, Araceli G. [1 ]
机构
[1] Univ Granada UGR, Dept Quim Organ, Granada 18071, Spain
基金
欧洲研究理事会;
关键词
POLYCYCLIC AROMATIC-HYDROCARBONS; CIRCULARLY-POLARIZED LUMINESCENCE; HEXA-PERI-HEXABENZOCORONENE; CYCLOHEPTATRIENE RING FORMATION; AGGREGATION-INDUCED EMISSION; GRAPHENE QUANTUM DOTS; CARBON-CARBON BONDS; SCHOLL REACTION; TRIBENZOTRIQUINACENE CORE; WARPED NANOGRAPHENE;
D O I
10.1039/c8cc02325e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This feature article focuses on the bottom-up approaches (solution-phase) based on organic synthesis for the preparation of saddle-shaped distorted polycyclic aromatic hydrocarbons (PAHs). We summarise the recent progress on the synthetic strategies followed to obtain well-defined nanographenes containing heptagonal and octagonal carbocycles, highlighting the novel strategy developed by our group together with our recent contributions in the area of distorted aromatics. The presence of seven- or eight-membered rings induces a saddle-shape curvature in the planar network pushing the structure out of the plane, which influences the physical properties exhibited. Some brief details on the optical and electronic properties of these curved nanostructures are also discussed.
引用
收藏
页码:6705 / 6718
页数:14
相关论文
共 132 条
[1]  
Banhart F, 2011, ACS NANO, V5, P26, DOI [10.1021/nn102598m, 10.1016/B978-0-08-102053-1.00005-3]
[2]   Chiral Nanographene Propeller Embedding Six Enantiomerically Stable [5]Helicene Units [J].
Berezhnaia, Veronika ;
Roy, Myriam ;
Vanthuyne, Nicolas ;
Villa, Marco ;
Naubron, Jean-Valere ;
Rodriguez, Jean ;
Coquerel, Yoann ;
Gingras, Marc .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (51) :18508-18511
[3]   A C216-Nanographene Molecule with Defined Cavity as Extended Coronoid [J].
Beser, Uliana ;
Kastler, Marcel ;
Maghsoumi, Ali ;
Wagner, Manfred ;
Castiglioni, Chiara ;
Tommasini, Matteo ;
Narita, Akimitsu ;
Feng, Xinliang ;
Muellen, Klaus .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (13) :4322-4325
[4]   Grain boundaries in graphene grown by chemical vapor deposition [J].
Biro, Laszlo P. ;
Lambin, Philippe .
NEW JOURNAL OF PHYSICS, 2013, 15
[5]   CRYSTAL-STRUCTURE OF OCTAMETHYLCYCLOOCTATETRAENE [J].
BORDNER, J ;
STANFORD, RH ;
PARKER, RG .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1972, B 28 (APR15) :1069-&
[6]   From Nanographene and Graphene Nanoribbons to Graphene Sheets: Chemical Synthesis [J].
Chen, Long ;
Hernandez, Yenny ;
Feng, Xinliang ;
Muellen, Klaus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (31) :7640-7654
[7]   A Twisted Nanographene Consisting of 96 Carbon Atoms [J].
Cheung, Kwan Yin ;
Chan, Chi Kit ;
Liu, Zhifeng ;
Miao, Qian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (31) :9003-9007
[8]   Aromatic Saddles Containing Two Heptagons [J].
Cheung, Kwan Yin ;
Xu, Xiaomin ;
Miao, Qian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (11) :3910-3914
[9]   THE ELECTRONIC INTERACTION BETWEEN BENZENOID RINGS IN CONDENSED AROMATIC HYDROCARBONS - 1,12-2,3-4,5-6,7-8,9-10,11-HEXABENZOCORONENE, 1,2-3,4-5,6-10,11-TETRABENZOANTHANTHRENE, AND 4,5-6,7-11,12-13,14-TETRABENZOPEROPYRENE [J].
CLAR, E ;
IRONSIDE, CT ;
ZANDER, M .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (JAN) :142-147
[10]   Metal-catalyzed activation of ethers via C-O bond cleavage: a new strategy for molecular diversity [J].
Cornella, Josep ;
Zarate, Cayetana ;
Martin, Ruben .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (23) :8081-8097