Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivative
A chromogenic trefoil-shaped salicylaldehyde azine derivative displayed solvent-dependent isomerism of the C3h and CS symmetries. An azine derivative was prepared from triformylphloroglucinol and 3,5-di-tert-butylsalicylaldehyde hydrazone. The trefoil structure was established using single-crystal X...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2023-12-01
|
| Series: | Results in Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715623004034 |
| _version_ | 1797398613229305856 |
|---|---|
| author | Masaya Naito Noriho Taniguchi Shinobu Miyagawa Hikaru Takaya Yuji Tokunaga |
| author_facet | Masaya Naito Noriho Taniguchi Shinobu Miyagawa Hikaru Takaya Yuji Tokunaga |
| author_sort | Masaya Naito |
| collection | DOAJ |
| description | A chromogenic trefoil-shaped salicylaldehyde azine derivative displayed solvent-dependent isomerism of the C3h and CS symmetries. An azine derivative was prepared from triformylphloroglucinol and 3,5-di-tert-butylsalicylaldehyde hydrazone. The trefoil structure was established using single-crystal X-ray diffraction. UV–vis absorption spectroscopy revealed that solvent-dependent isomerization was accompanied by a bathochromic shift. Isomerization was controlled by adjusting the strength of the intramolecular hydrogen bonding of the azine derivative by solvent polarity. This unusual solvent-dependent isomerization can be utilized for creation azine-based new solvatochromic materials. |
| first_indexed | 2024-03-09T01:28:05Z |
| format | Article |
| id | doaj.art-24a9555cd7524bf3b1c8b18ff4f9e021 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-03-09T01:28:05Z |
| publishDate | 2023-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-24a9555cd7524bf3b1c8b18ff4f9e0212023-12-10T06:15:28ZengElsevierResults in Chemistry2211-71562023-12-016101164Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivativeMasaya Naito0Noriho Taniguchi1Shinobu Miyagawa2Hikaru Takaya3Yuji Tokunaga4Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan; Corresponding authors.Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, JapanDepartment of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, JapanDepartment of Life and Health Sciences, Faculty of Life and Environmental Sciences, Teikyo University of Science, Adachi-ku, Tokyo 120-0045, Japan; Institute for Molecular Science, National Institute of Natural Science, Okazaki, Aichi 444-8585, JapanDepartment of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan; Corresponding authors.A chromogenic trefoil-shaped salicylaldehyde azine derivative displayed solvent-dependent isomerism of the C3h and CS symmetries. An azine derivative was prepared from triformylphloroglucinol and 3,5-di-tert-butylsalicylaldehyde hydrazone. The trefoil structure was established using single-crystal X-ray diffraction. UV–vis absorption spectroscopy revealed that solvent-dependent isomerization was accompanied by a bathochromic shift. Isomerization was controlled by adjusting the strength of the intramolecular hydrogen bonding of the azine derivative by solvent polarity. This unusual solvent-dependent isomerization can be utilized for creation azine-based new solvatochromic materials.http://www.sciencedirect.com/science/article/pii/S2211715623004034Solvent-dependent isomerizationSalicylaldehyde azine derivativeChromogensMolecular sensors |
| spellingShingle | Masaya Naito Noriho Taniguchi Shinobu Miyagawa Hikaru Takaya Yuji Tokunaga Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivative Results in Chemistry Solvent-dependent isomerization Salicylaldehyde azine derivative Chromogens Molecular sensors |
| title | Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivative |
| title_full | Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivative |
| title_fullStr | Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivative |
| title_full_unstemmed | Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivative |
| title_short | Solvent-dependent isomerization of a chromogenic trefoil-shaped salicylaldehyde azine derivative |
| title_sort | solvent dependent isomerization of a chromogenic trefoil shaped salicylaldehyde azine derivative |
| topic | Solvent-dependent isomerization Salicylaldehyde azine derivative Chromogens Molecular sensors |
| url | http://www.sciencedirect.com/science/article/pii/S2211715623004034 |
| work_keys_str_mv | AT masayanaito solventdependentisomerizationofachromogenictrefoilshapedsalicylaldehydeazinederivative AT norihotaniguchi solventdependentisomerizationofachromogenictrefoilshapedsalicylaldehydeazinederivative AT shinobumiyagawa solventdependentisomerizationofachromogenictrefoilshapedsalicylaldehydeazinederivative AT hikarutakaya solventdependentisomerizationofachromogenictrefoilshapedsalicylaldehydeazinederivative AT yujitokunaga solventdependentisomerizationofachromogenictrefoilshapedsalicylaldehydeazinederivative |