Supramolecular dye inclusion single crystals created from 2,3,6-Trimethyl-β-cyclodextrin and porphyrins

Youichi Tsuchiya, Tomohiro Shiraki, Takashi Matsumoto, Kouta Sugikawa, Kazuki Sada, Akihito Yamano, Seiji Shinkai

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

In Nature, chromophoric groups play various roles, such as oxygen carriers, electron donors, light sensitizers, which are achieved in many cases by control of their aggregation modes in proteins. Host-guest chemistry between cyclodextrins and porphyrins has attracted great interest from supramolecular chemists because of their unique structures and functions that mimic those of proteins with chromophoric prosthetic groups. To mimic Nature's contrivances, the host-guest systems between cyclodextrins and porphyrins have frequently been studied. It is really surprising, however, that to date no detailed structural information of these complexes has been obtained from single-crystal analysis. In 2011, we reported the first successful isolation of a dye inclusion single crystal (DISC) between 2,3,6-trimethyl-β-cyclodextrin (TMβCD) and 5,10,15,20-tetrapyridylporphyrin (TPyP), and analyzed its X-ray crystal structure. The crystal structure revealed not only the real complex mode but also the attractive orientation of TPyP in the DISC. Herein, we present new strategies to prepare DISCs of TMβCD for several porphyrins and provide crystal structures, details of the complex modes, and optical properties. We believe that the present study has various important implications not only for the basic crystal analysis of inclusion complexes but also for potential applications that use these single crystals.

Original languageEnglish
Pages (from-to)456-465
Number of pages10
JournalChemistry - A European Journal
Volume18
Issue number2
DOIs
Publication statusPublished - Jan 9 2012

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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