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Yang, Changduk
Advanced Tech-Optoelectronic Materials Synthesis Lab (ATOMS)
Research Interests
  • Optoelectronic materials synthesis/organic electronics, functionalization of carbonaceous solids, advanced materials chemistry, macromolecular chemistry

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An unprecedented [5,6]-open adduct via a direct benzyne-C-60 cycloaddition

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Title
An unprecedented [5,6]-open adduct via a direct benzyne-C-60 cycloaddition
Author
Kim, GyoungsikLee, Kyu CheolKim, JonggiLee, Jeong ChulLee, Sang MyeonLee, Jeong ChuSeo, Jung HwaChoi, Won-YoulYang, Changduk
Keywords
[5,6]-Open adduct; [6,6]-Closed adduct; Benzyne; Buckminsterfullerene; Cycloaddition
Issue Date
201309
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Citation
TETRAHEDRON, v.69, no.35, pp.7354 - 7359
Abstract
Cycloaddition is one of the best-studied types of reactions in the organic chemistry of fullerenes, engendering [6,6]-closed adducts in the vast majority of cases. Notwithstanding that a formation of open fulleroid structures is undoubtedly of theoretical interest, no one has demonstrated the conformation of [5,6]-open fulleroid via the direct cycloadditions. Here, we establish that cycloaddition between C60 and benzyne in situ generated from 2-amino-4,5-dibutoxybenzoic acid affords a new type of elusive [5,6]-open structure that is characterized on the basis of NMR, UV-vis spectroscopy, and cyclic voltammetry. Additionally, from density functional theory (DFT) calculations for possible [5,6]-open and [6,6]-closed adducts induced of benzyne-C60 reaction, as expected, features such as the charge distributions, binding characteristics, and frontier molecular orbital levels, are affected by the different binding modes in C60 cage.
URI
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DOI
http://dx.doi.org/10.1016/j.tet.2013.06.073
ISSN
0040-4020
Appears in Collections:
ECHE_Journal Papers
SNS_Journal Papers

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