An unprecedented [5,6]-open adduct via a direct benzyne-C60 cycloaddition

Gyoungsik Kim, Kyu Cheol Lee, Jonggi Kim, Jungho Lee, Sang Myeon Lee, Jeong Chul Lee, Jung Hwa Seo, Won Youl Choi, Changduk Yang

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

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.

Original languageEnglish
Pages (from-to)7354-7359
Number of pages6
JournalTetrahedron
Volume69
Issue number35
DOIs
StatePublished - 2 Sep 2013

Keywords

  • Benzyne
  • Buckminsterfullerene
  • Cycloaddition
  • [5,6]-Open adduct
  • [6,6]-Closed adduct

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