An Electrochemically Controllable Nanomechanical Molecular System Utilizing Edge-to-Face and Face-to-Face Aromatic Interactions

Heon Gon Kim, Chi Wan Lee, Sunggoo Yun, Byung Hee Hong, Young Ok Kim, Dongwook Kim, Hyejae Ihm, Jung Woo Lee, Eun Cheol Lee, P. Tarakeshwar, Su Moon Park, Kwang S. Kim

Research output: Contribution to journalArticle

56 Scopus citations

Abstract

(Matrix Presented) A new molecular system, 2,11-dithio[4,4]metametaquinocyclophane containing a quinone moiety, was designed and synthesized. As the quinone moiety can readily be converted into an aromatic π-system (hydroquinone) upon reduction, the nanomechanical molecular cyclophane system exhibits a large flapping motion like a molecular flipper from the electrochemical redox process. The conformational changes upon reduction and oxidation are caused by changes of nonbonding interaction forces (devoid of bond formation/breaking) from the edge-to-face to face-to-face aromatic interactions and vice versa, respectively.

Original languageEnglish (US)
Pages (from-to)3971-3974
Number of pages4
JournalOrganic Letters
Volume4
Issue number22
DOIs
StatePublished - Oct 31 2002
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Kim, H. G., Lee, C. W., Yun, S., Hong, B. H., Kim, Y. O., Kim, D., Ihm, H., Lee, J. W., Lee, E. C., Tarakeshwar, P., Park, S. M., & Kim, K. S. (2002). An Electrochemically Controllable Nanomechanical Molecular System Utilizing Edge-to-Face and Face-to-Face Aromatic Interactions. Organic Letters, 4(22), 3971-3974. https://doi.org/10.1021/ol0268541