Molecular design for a write-by-light/erase-by-heat recording system using photochromic diarylethenes with thermal cycloreversion. Issue 35 (30th August 2019)

• Record Type: Journal Article
• Authors: Sato, Yuta; Kitagawa, Daichi; Kobatake, Seiya
• Is Part Of: Tetrahedron. Volume 75:Issue 35(2019)
• Publication Date: 2019-08-30
• Subjects: Photochromism -- Diarylethene -- Substituent effect -- Thermal reactivity -- Substituent constant; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.130487
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: We designed and synthesized photochromic diarylethenes for a write-by-light/erase-by-heat recording system. The introduction of polar substituents at both sides of the diarylethene maintained the photocyclization and photocycloreversion reactivities, but significantly affected the thermal cycloreversion reactivity. The introduction of electron-withdrawing substituents accelerated the thermal reaction and the introduction of electron-donating substituents suppressed the thermal reaction. The rate constants of the thermal reaction were well correlated with Brown-Okamoto's substituent constant σ + that is a modified value of Hammett's substituent constant σ. The large rate constants are ascribed to the lower activation energy for the thermal reaction. These results provide new knowledge for the molecular design of diarylethenes for a write-by-light/erase-by-heat recording system. Graphical abstract: Image 1 Highlights: We designed photochromic diarylethenes for a write-by-light/erase-by-heat recording system. Diarylethenes having polar substituents at both sides were newly synthesized. Photocyclization and photocycloreversion quantum yields remained constant even in the introduction of the polar substituents. Thermal cycloreversion reactivities were significantly accelerated by introduction of the electron-withdrawing substituents. We demonstrated a write-by-light/erase-by-heat recording system in the filter paper with the ability to erase even at 120 °C.