Two-dimensional supramolecular arrangements of enantiomers and racemic modification of 1,1′-binaphthyl-2,2′-dicarboxylic acid

Masashi Kunitake, Tetsutaro Hattori, Sotaro Miyano, Kingo Itaya

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

Formation of adlayers of the optically active compound 1,1′- binaphthyl-2, 2′-dicarboxylic acid (BINAC) on iodine-modified Au (111) surfaces in perchloric acid was investigated by in situ scanning tunneling microscopy (STM). Highly ordered arrays formed on the surfaces via simple spontaneous adsorption from a solution of enantiomers or the racemic BINAC, in spite of the fact that BINAC has a three-dimensionally complex stereochemical structure. Adlayers of both enantiomers essentially shared the same enantiomorphous structure. Observed parameters of the rectangular unit cell lattice for arrays of both enantiomers of BINAC were a = 2.3 ± 0.2 nm and b = 0.7 ± 0.2 nm. On the other hand, racemic modification formed an entirely different adlayer, which consisted of an alternate alignment of the two enantiomers, with an oblique unit cell lattice with parameters of a = 1.2 ± 0.2 nm, b = 0.8 ± 0.1 nm, and 74 ± 3°. No domain composed of a single enantiomer was observed. The stronger hetero-intermolecular interactions of enantiomer couples led to the formation of an alternate arrangement in the array prepared by racemic modification.

Original languageEnglish
Pages (from-to)9206-9210
Number of pages5
JournalLangmuir
Volume21
Issue number20
DOIs
Publication statusPublished - 2005 Sep 27

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

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