Computational assessment of 1,3-dipolar cycloadditions to graphene

被引：54

作者：

Cao, Yang ^{[1
]}

Houk, K. N. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF MATERIALS CHEMISTRY | 2011年 / 21卷 / 05期

关键词：

WALLED CARBON NANOTUBES; CYANO-CIS-STILBENE; TETRACYANOETHYLENE OXIDE; PERICYCLIC-REACTIONS; ACTIVATION BARRIERS; REACTION ENERGETICS; AZOMETHINE YLIDES; CBS-QB3; METHODS; STANDARD SET; FUNCTIONALIZATION;

D O I：

10.1039/c0jm02422h

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The 1,3-dipolar cycloadditions of azomethine ylide and carbonyl ylide to models of graphene have been investigated with density functional theory. Reaction energetics have been obtained and show that edge areas of graphene are much more favourable reaction sites than the centre sites. Azomethine ylide cannot directly react at the centre area, while carbonyl ylides are promising reagents for functionalization of graphene. The influence of some 1,3-dipole substituents is also evaluated.

引用

页码：1503 / 1508

页数：6

共 58 条

[1] Honeycomb Carbon: A Review of Graphene [J].

Allen, Matthew J. ;

Tung, Vincent C. ;

Kaner, Richard B. .

CHEMICAL REVIEWS, 2010, 110 (01) :132-145

[2] Oligoacenes: Theoretical prediction of open-shell singlet diradical ground states [J].

Bendikov, M ;

Duong, HM ;

Starkey, K ;

Houk, KN ;

Carter, EA ;

Wudl, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7416-7417

[3] Fullerene derivatives: an attractive tool for biological applications [J].

Bosi, S ;

Da Ros, T ;

Spalluto, G ;

Prato, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (11-12) :913-923

[4] The 1,3 Dipolar Cycloaddition of Azomethine Ylides to Graphene, Single Wall Carbon Nanotubes, and C60 [J].

Denis, Pablo A. ;

Iribarne, Federico .

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2010, 110 (09) :1764-1771

[5] Optical properties of C-60 and related materials [J].

Dresselhaus, MS ;

Dresselhaus, G ;

Rao, AM ;

Eklund, PC .

SYNTHETIC METALS, 1996, 78 (03) :313-325

[6] Covalent functionalization of single-walled carbon nanotubes for materials applications [J].

Dyke, CA ;

Tour, JM .

JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (51) :11151-11159

[7] Overcoming the insolubility of carbon nanotubes through high degrees of sidewall functionalization [J].

Dyke, CA ;

Tour, JM .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (04) :813-817

[8] Theory of 1,3-dipolar cycloadditions: Distortion/interaction and frontier molecular orbital models [J].

Ess, Daniel H. ;

Houk, K. N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) :10187-10198

[9] Distortion/Interaction energy control of 1,3-dipolar cycloaddition reactivity [J].

Ess, Daniel H. ;

Houk, K. N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (35) :10646-+

[10] Activation energies of pericyclic reactions: Performance of DFT, MP2, and CBS-QB3 methods for the prediction of activation barriers and reaction energetics of 1,3-dipolar cycloadditions, and revised activation enthalpies for a standard set of hydrocarbon pericyclic reactions [J].

Ess, DH ;

Houk, KN .

JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (42) :9542-9553

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