Reversible diastereoselective photocyclization of a diarylethene in a single-crystalline phase

T. Kodani, K. Matsuda, Teppei Yamada, S. Kobatake, M. Irie

Research output: Contribution to journalArticle

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Abstract

Optically active photochromic (S)- and (R)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3- thienyl]-3,3,4,4,5,5-hexafluorocyclopentenes ((S)-1a and (R)-1a) were synthesized. X-ray crystallographic measurement showed that (S)-1a and (R)-1a single crystals adopted orthorhombic chiral space group P212121 and the open-ring isomers were packed in the crystals in only one conformer of the possible two atropisomers. Upon irradiation with 366 nm light (S)-1a and (R)-1a underwent reversible photocyclization reactions both in solution and in the single-crystalline state, and in the crystalline phase almost only one closed-ring diastereomer was produced, while the diastereoselection was not observed in solution. The dominant diastereomer produced from (S)-1a was determined to be (S,R,R)-1b by X-ray crystallographic analysis.

Original languageEnglish
Pages (from-to)9631-9637
Number of pages7
JournalJournal of the American Chemical Society
Volume122
Issue number40
DOIs
Publication statusPublished - Oct 11 2000

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X-Rays
Crystalline materials
X rays
Isomers
Irradiation
Single crystals
Light
Crystals
1,21-diamino-4,9,13,18-tetraazahenicosane

All Science Journal Classification (ASJC) codes

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

Cite this

Reversible diastereoselective photocyclization of a diarylethene in a single-crystalline phase. / Kodani, T.; Matsuda, K.; Yamada, Teppei; Kobatake, S.; Irie, M.

In: Journal of the American Chemical Society, Vol. 122, No. 40, 11.10.2000, p. 9631-9637.

Research output: Contribution to journalArticle

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AU - Matsuda, K.

AU - Yamada, Teppei

AU - Kobatake, S.

AU - Irie, M.

PY - 2000/10/11

Y1 - 2000/10/11

N2 - Optically active photochromic (S)- and (R)-1-(2-methyl-5-phenyl-3-thienyl)-2-[2-(3-methyl-1-penten-1-yl)-5-phenyl-3- thienyl]-3,3,4,4,5,5-hexafluorocyclopentenes ((S)-1a and (R)-1a) were synthesized. X-ray crystallographic measurement showed that (S)-1a and (R)-1a single crystals adopted orthorhombic chiral space group P212121 and the open-ring isomers were packed in the crystals in only one conformer of the possible two atropisomers. Upon irradiation with 366 nm light (S)-1a and (R)-1a underwent reversible photocyclization reactions both in solution and in the single-crystalline state, and in the crystalline phase almost only one closed-ring diastereomer was produced, while the diastereoselection was not observed in solution. The dominant diastereomer produced from (S)-1a was determined to be (S,R,R)-1b by X-ray crystallographic analysis.

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