Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

Aza-diarylethene has been developed as a new family of photochromic compounds. This study explores the photochromic properties and thermal back reactivities of various aza-diarylethene regioisomers (N1–N4 and I1–I4) in n-hexane. These molecules exhibit fast thermally reversible photochromic reaction...

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Main Authors: Misato Suganuma, Daichi Kitagawa, Shota Hamatani, Seiya Kobatake
Format: Article
Language:English
Published: Beilstein-Institut 2025-01-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.21.16
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author Misato Suganuma
Daichi Kitagawa
Shota Hamatani
Seiya Kobatake
author_facet Misato Suganuma
Daichi Kitagawa
Shota Hamatani
Seiya Kobatake
author_sort Misato Suganuma
collection DOAJ
description Aza-diarylethene has been developed as a new family of photochromic compounds. This study explores the photochromic properties and thermal back reactivities of various aza-diarylethene regioisomers (N1–N4 and I1–I4) in n-hexane. These molecules exhibit fast thermally reversible photochromic reactions driven by 6π aza-electrocyclization. Kinetic analysis of the thermal back reaction revealed activation parameters, highlighting how the substitution position of the aryl group affects the thermal stability. Additionally, density functional theory calculations identified M06 and MPW1PW91 as the most accurate functionals for predicting the thermal back reactivity, closely matching the experimental data. These findings offer valuable insights for the design of advanced photochromic materials with tailored thermal and photophysical characteristics.
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institution Kabale University
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publisher Beilstein-Institut
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series Beilstein Journal of Organic Chemistry
spelling doaj-art-8a8f11e6c9da49ce8b390ecd7ba2017e2025-02-03T09:10:18ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-01-0121124225210.3762/bjoc.21.161860-5397-21-16Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theoryMisato Suganuma0Daichi Kitagawa1Shota Hamatani2Seiya Kobatake3Department of Chemistry and Bioengineering, Graduate School of Engineering, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan Department of Chemistry and Bioengineering, Graduate School of Engineering, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan Department of Chemistry and Bioengineering, Graduate School of Engineering, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan Department of Chemistry and Bioengineering, Graduate School of Engineering, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan Aza-diarylethene has been developed as a new family of photochromic compounds. This study explores the photochromic properties and thermal back reactivities of various aza-diarylethene regioisomers (N1–N4 and I1–I4) in n-hexane. These molecules exhibit fast thermally reversible photochromic reactions driven by 6π aza-electrocyclization. Kinetic analysis of the thermal back reaction revealed activation parameters, highlighting how the substitution position of the aryl group affects the thermal stability. Additionally, density functional theory calculations identified M06 and MPW1PW91 as the most accurate functionals for predicting the thermal back reactivity, closely matching the experimental data. These findings offer valuable insights for the design of advanced photochromic materials with tailored thermal and photophysical characteristics.https://doi.org/10.3762/bjoc.21.16aza-diarylethenedft calculationphotochromismpredictionthermal back reactivity
spellingShingle Misato Suganuma
Daichi Kitagawa
Shota Hamatani
Seiya Kobatake
Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory
Beilstein Journal of Organic Chemistry
aza-diarylethene
dft calculation
photochromism
prediction
thermal back reactivity
title Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory
title_full Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory
title_fullStr Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory
title_full_unstemmed Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory
title_short Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory
title_sort effect of substitution position of aryl groups on the thermal back reactivity of aza diarylethene photoswitches and prediction by density functional theory
topic aza-diarylethene
dft calculation
photochromism
prediction
thermal back reactivity
url https://doi.org/10.3762/bjoc.21.16
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AT daichikitagawa effectofsubstitutionpositionofarylgroupsonthethermalbackreactivityofazadiarylethenephotoswitchesandpredictionbydensityfunctionaltheory
AT shotahamatani effectofsubstitutionpositionofarylgroupsonthethermalbackreactivityofazadiarylethenephotoswitchesandpredictionbydensityfunctionaltheory
AT seiyakobatake effectofsubstitutionpositionofarylgroupsonthethermalbackreactivityofazadiarylethenephotoswitchesandpredictionbydensityfunctionaltheory