Oligonaphthofurans: Fan-shaped and three-dimensional π-compounds

Kentaro Nakanishi, Daisuke Fukatsu, Kazuto Takaishi, Taiki Tsuji, Keita Uenaka, Kouji Kuramochi, Takeo Kawabata, Kazunori Tsubaki

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

Using a bottom-up method, we prepared a series of oligonaphthofurans composed of alternating naphthalene rings and furan rings. The largest compound (compound 25) contained 8 naphthalene units and 7 furan units. DFT calculations revealed that these compounds were fan-shaped molecules and each naphthalene ring was oriented in an alternate mountain-valley fold conformation because of steric repulsion by the hydrogens at the peri-positions. We investigated the optical properties that derived from their fan-shaped and mountain-valley sequences. As the number of aromatic rings of the oligonaphthofurans increased, the peaks of the longest wavelength absorptions in the UV-vis spectra (HOMO-LUMO energy gap) of these compounds steadily red-shifted, although the shapes of spectra were not sustained because of the decreasing molar absorption coefficients (εs) of their λmax. We compared our results with those reported for other types of oligoaromatic compounds such as acenes 1, ethene-bridged p-phenylenes 2, rylenes 3, oligofurans 4, and oligonaphthalenes 5. The slopes of the plots between the transition energies (HOMO-LUMO energy gap) of the oligoaromatic compounds and the reciprocal of the number of aromatic rings indicated that the efficiency of π conjugation of the oligonaphthofurans was comparable with that of linear and rigid acenes and rylenes. The higher-order compounds 22 and 25 aggregated even under high dilution conditions (∼10-6 M).

Original languageEnglish
Pages (from-to)7101-7109
Number of pages9
JournalJournal of the American Chemical Society
Volume136
Issue number19
DOIs
Publication statusPublished - May 14 2014
Externally publishedYes

Fingerprint

Naphthalene
Fans
Energy gap
Electron transitions
Discrete Fourier transforms
Dilution
Conformations
Hydrogen
Optical properties
Wavelength
Molecules
naphthalene
furan

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Nakanishi, K., Fukatsu, D., Takaishi, K., Tsuji, T., Uenaka, K., Kuramochi, K., ... Tsubaki, K. (2014). Oligonaphthofurans: Fan-shaped and three-dimensional π-compounds. Journal of the American Chemical Society, 136(19), 7101-7109. https://doi.org/10.1021/ja502209w

Oligonaphthofurans : Fan-shaped and three-dimensional π-compounds. / Nakanishi, Kentaro; Fukatsu, Daisuke; Takaishi, Kazuto; Tsuji, Taiki; Uenaka, Keita; Kuramochi, Kouji; Kawabata, Takeo; Tsubaki, Kazunori.

In: Journal of the American Chemical Society, Vol. 136, No. 19, 14.05.2014, p. 7101-7109.

Research output: Contribution to journalArticle

Nakanishi, K, Fukatsu, D, Takaishi, K, Tsuji, T, Uenaka, K, Kuramochi, K, Kawabata, T & Tsubaki, K 2014, 'Oligonaphthofurans: Fan-shaped and three-dimensional π-compounds', Journal of the American Chemical Society, vol. 136, no. 19, pp. 7101-7109. https://doi.org/10.1021/ja502209w
Nakanishi, Kentaro ; Fukatsu, Daisuke ; Takaishi, Kazuto ; Tsuji, Taiki ; Uenaka, Keita ; Kuramochi, Kouji ; Kawabata, Takeo ; Tsubaki, Kazunori. / Oligonaphthofurans : Fan-shaped and three-dimensional π-compounds. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 19. pp. 7101-7109.
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