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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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| 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. |
| format | Article |
| id | doaj-art-8a8f11e6c9da49ce8b390ecd7ba2017e |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| 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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