Dibenzosuberenone-Based Photo- and Thermochromic Switches, a Transformation: Rearrangement of Dibenzosuberenones to Spiro Anthrones

Kocak R., DAŞTAN A.

ORGANIC LETTERS, cilt.23, sa.11, ss.4483-4487, 2021 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 23 Sayı: 11
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1021/acs.orglett.1c01413
  • Dergi Adı: ORGANIC LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Chemical Abstracts Core, Chimica, EMBASE, MEDLINE
  • Sayfa Sayıları: ss.4483-4487
  • Atatürk Üniversitesi Adresli: Evet

Özet

In this study, a new class of photo- and thermochromic compounds was discovered. Fluorescent dihydropyridazine-appended dibenzosuberenone derivatives with central seven-membered rings were converted to colorless spiro anthrones with central six-membered rings by thermal isomerization or visible-light (420 nm) irradiation. Under UV light (350 nm), the spiro anthrones converted back to benzosuberenones. The chemical structures of the spiro anthrones were determined by NMR, UV-vis spectroscopy, and HRMS analyses. It was also observed that the dibenzosuberenone derivatives were oxidized on exposure to UV irradiation for a long time.