Tunable Solid-State Thermochromism: Alkyl Chain Length-Dependent Conformational Isomerization of Bianthrones.

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  • Additional Information
    • Source:
      Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101294643 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1861-471X (Electronic) Linking ISSN: 1861471X NLM ISO Abbreviation: Chem Asian J Subsets: MEDLINE
    • Publication Information:
      Original Publication: Weinheim, Germany : Wiley-VCH, c2006-
    • Subject Terms:
      Isomerism*; Anthracenes ; Molecular Conformation ; Powders ; Spectroscopy, Fourier Transform Infrared
    • Abstract:
      The introduction of linear alkoxy chains into bianthrone promoted the aggregation of the minor twisted conformer and made it compete with the major folded conformer in the solid-state. Rapid evaporation approach to the methoxy- and n-butoxy-substituted derivatives provided powder mixtures of folded and twisted conformers as metastable solids. Upon heating the powders, different lengths of alkyl chains converged to different conformers via solid-state isomerization reaction with an apparent color change. Monitoring by FT-IR spectroscopy and powder XRD ensured that these isomerization reactions involve only conformational isomerization without pyrolysis. In addition, single crystal X-ray structure analysis revealed that twisted conformers with longer alkyl chains are stabilized in the solid-state by the synergistic effect of their inter-chain hydrophobic interactions and π-π stacking interactions.
      (© 2022 Wiley-VCH GmbH.)
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    • Grant Information:
      JP18K05079 JSPS KAKENHI; JP15H00942 JSPS KAKENHI
    • Contributed Indexing:
      Keywords: Crystal growth; Isomerization; Solid-state reactions; Strained molecules; Thermochromism
    • Accession Number:
      0 (Anthracenes)
      0 (Powders)
      434-85-5 (bianthrone)
    • Publication Date:
      Date Created: 20220407 Date Completed: 20220602 Latest Revision: 20220602
    • Publication Date:
      20221213
    • Accession Number:
      10.1002/asia.202200121
    • Accession Number:
      35388961