Effect of substituted β-cyclodextrins on the kinetics of the photochromic processes and hydrolysis of trans-merocyanine
The effect of β-cyclodextrin (βCD) and its 2-hydroxypropyl, sulfate, and sulfobutyl derivatives was studied to reveal how the host-guest binding influenced the reversible photochromic reactions and the hydrolysis of a trans-merocyanine (trans-MC) dye in acidic and neutral aqueous solutions. Absorpti...
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| Format: | Article |
| Language: | English |
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Elsevier
2025-03-01
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| Series: | Carbohydrate Polymer Technologies and Applications |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666893925000684 |
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| author | Zsombor Miskolczy Mónika Megyesi Gábor Turczel László Biczók |
| author_facet | Zsombor Miskolczy Mónika Megyesi Gábor Turczel László Biczók |
| author_sort | Zsombor Miskolczy |
| collection | DOAJ |
| description | The effect of β-cyclodextrin (βCD) and its 2-hydroxypropyl, sulfate, and sulfobutyl derivatives was studied to reveal how the host-guest binding influenced the reversible photochromic reactions and the hydrolysis of a trans-merocyanine (trans-MC) dye in acidic and neutral aqueous solutions. Absorption, fluorescence, and NMR spectroscopic measurements demonstrated that the protonated trans-merocyanine (trans-MCH+) produced 1:1 inclusion complex with sulfobutylether- or sulfate-substituted βCD, but the association did not occur with βCD and its 2-hydroxypropyl derivative at pH 2.3. Therefore, only the former cavitands accelerated the photoinduced transformation to the spiropyran (SP) isomer. In contrast, SP was encapsulated in each examined host, and the thermal back conversion from SP to trans-MCH+ was slower within the macrocycles than in water. The unprotonated trans-MC was not incorporated in sulfate-substituted βCD, but the weak complexation with the other employed βCD derivatives catalyzed the hydrolysis of the guest dye at pH 7. |
| format | Article |
| id | doaj-art-16fd03c1936249d7b0d080120ce29ded |
| institution | DOAJ |
| issn | 2666-8939 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Carbohydrate Polymer Technologies and Applications |
| spelling | doaj-art-16fd03c1936249d7b0d080120ce29ded2025-08-20T02:52:21ZengElsevierCarbohydrate Polymer Technologies and Applications2666-89392025-03-01910072910.1016/j.carpta.2025.100729Effect of substituted β-cyclodextrins on the kinetics of the photochromic processes and hydrolysis of trans-merocyanineZsombor Miskolczy0Mónika Megyesi1Gábor Turczel2László Biczók3Institute of Materials and Environmental Chemistry, HUN-REN Research Centre for Natural Sciences, , P.O. Box 286, 1519 Budapest, HungaryInstitute of Materials and Environmental Chemistry, HUN-REN Research Centre for Natural Sciences, , P.O. Box 286, 1519 Budapest, HungaryNMR Research Laboratory, Centre for Structural Science, HUN-REN Research Centre for Natural Sciences, P.O. Box 286, 1519 Budapest, HungaryInstitute of Materials and Environmental Chemistry, HUN-REN Research Centre for Natural Sciences, , P.O. Box 286, 1519 Budapest, Hungary; Corresponding author.The effect of β-cyclodextrin (βCD) and its 2-hydroxypropyl, sulfate, and sulfobutyl derivatives was studied to reveal how the host-guest binding influenced the reversible photochromic reactions and the hydrolysis of a trans-merocyanine (trans-MC) dye in acidic and neutral aqueous solutions. Absorption, fluorescence, and NMR spectroscopic measurements demonstrated that the protonated trans-merocyanine (trans-MCH+) produced 1:1 inclusion complex with sulfobutylether- or sulfate-substituted βCD, but the association did not occur with βCD and its 2-hydroxypropyl derivative at pH 2.3. Therefore, only the former cavitands accelerated the photoinduced transformation to the spiropyran (SP) isomer. In contrast, SP was encapsulated in each examined host, and the thermal back conversion from SP to trans-MCH+ was slower within the macrocycles than in water. The unprotonated trans-MC was not incorporated in sulfate-substituted βCD, but the weak complexation with the other employed βCD derivatives catalyzed the hydrolysis of the guest dye at pH 7.http://www.sciencedirect.com/science/article/pii/S2666893925000684CyclodextrinInclusion complexesPhotochromismKineticsPhotoisomerizationCatalysis |
| spellingShingle | Zsombor Miskolczy Mónika Megyesi Gábor Turczel László Biczók Effect of substituted β-cyclodextrins on the kinetics of the photochromic processes and hydrolysis of trans-merocyanine Carbohydrate Polymer Technologies and Applications Cyclodextrin Inclusion complexes Photochromism Kinetics Photoisomerization Catalysis |
| title | Effect of substituted β-cyclodextrins on the kinetics of the photochromic processes and hydrolysis of trans-merocyanine |
| title_full | Effect of substituted β-cyclodextrins on the kinetics of the photochromic processes and hydrolysis of trans-merocyanine |
| title_fullStr | Effect of substituted β-cyclodextrins on the kinetics of the photochromic processes and hydrolysis of trans-merocyanine |
| title_full_unstemmed | Effect of substituted β-cyclodextrins on the kinetics of the photochromic processes and hydrolysis of trans-merocyanine |
| title_short | Effect of substituted β-cyclodextrins on the kinetics of the photochromic processes and hydrolysis of trans-merocyanine |
| title_sort | effect of substituted β cyclodextrins on the kinetics of the photochromic processes and hydrolysis of trans merocyanine |
| topic | Cyclodextrin Inclusion complexes Photochromism Kinetics Photoisomerization Catalysis |
| url | http://www.sciencedirect.com/science/article/pii/S2666893925000684 |
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