Conformational Dynamics of Monomer- versus Dimer-like Features in a Naphthalenediimide-Based Conjugated Cyclophane

Sudhir Kumar Keshri, Atsuro Takai, Tomoya Ishizuka, Takahiko Kojima, Masayuki Takeuchi

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The design and synthesis of an enantiomeric pair of 1,8-diethynylanthracene-bridged naphthalenediimide (NDI)-based cyclophanes (Cyclo-NDIs) are reported. Each enantiomer of Cyclo-NDI exhibits a circularly polarized luminescence signal with a relatively large luminescence dissymmetry factor (glum=±8×10−3). We have further investigated the modulation of through-space electronic communication between co-facially oriented NDIs in a discrete Cyclo-NDI with changes in the temperature. Tuning of the electronic communication results from the conformational transformation of monomer- versus dimer-like features of Cyclo-NDI, as confirmed by UV/Vis, fluorescence, circular dichroic, and NMR spectroscopic analysis. The temperature-dependent optical response in the Cyclo-NDI through the conformational transformation could be utilized as a highly sensitive and reversible optical thermometer in a wide temperature range (100 to −80 °C).

Original languageEnglish
Pages (from-to)5254-5258
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number13
DOIs
Publication statusPublished - 2020 Mar 23
Externally publishedYes

Keywords

  • circularly polarized luminescence
  • conformational transformations
  • cyclophanes
  • naphthalenediimide dimers
  • optical thermometry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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