Synthesis and optical properties of the helical oligonaphthalenes

Kazuto Takaishi, Kazunori Tsubaki, Hiroyuki Tanaka, Masaya Miura, Takeo Kawabata

Research output: Contribution to journalReview article

7 Citations (Scopus)

Abstract

We have developed an efficient synthesis method for optically active oligonaphthalenes (from 2 mer to 16 mer), which are connected at their 1,4-positions, under oxidative homo coupling with a stoichiometric amount of CuCl2 and a-mines. The absolute configuration of the newly formed axis bond was determined based on the CD spectra of oligonaphthalenes with 1) two pyrene rings on the central naphthalenes or 2) two tetraphenylporphyrins (TPP) on the top and bottom naphthalenes. The fluorescence quantum yields increased as the number of naphthalene units increased in methoxy derivatives 10-12, and the intramolecular energy transfer quantum yields of bispyrene derivatives 7-9 were around 20% regardless of the number of naphthalene units. Furthermore, the hexadecanaphthalene derivative 4b with two TPPs exhibited a clear exciton coupling over an interchromophore distance to ca. 66 Å.

Original languageEnglish
Pages (from-to)779-787
Number of pages9
JournalYakugaku Zasshi
Volume126
Issue number9
DOIs
Publication statusPublished - Sep 15 2006
Externally publishedYes

Keywords

  • Bottom-up synthesis
  • Energy transfer
  • Long-range exciton coupling
  • Oligonaphthalenes

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

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