Salihovic, Demir (2025) 2,3-Disubstituted Indenone Photoswitches. Bachelor's Thesis, Chemistry.
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Abstract
Photochromic switches are molecules that isomerise upon being illuminated with light. Among these photochromic switches, some can isomerise not only in response to light but also in response to mechanical cues – these are called mechanophores. In this study, we investigate whether 2,3-disubstituted indenone epoxide (DIO) molecules can serve as mechanophores, given their previously reported photoreactivity, strained epoxide structure, and potential for selective bond cleavage under mechanical force. Therefore, we designed and synthesized two DIO-based switches, each bearing either a terminal vinyl or a primary alcohol group, allowing for their incorporation into PDMS and polyurethane (PU) film, respectively. These molecules were tested for their photo- and mechanoresponsiveness. Moreover, the critical force (Fcrit) required for C–C bond scission in the epoxide was estimated by DFT calculations. Overall, these findings offer insight into the structure–reactivity relationships governing DIO-based mechanophores, they broaden the toolbox of photochromes and mechanophores, and they provide a foundation for the design of mechano-responsive polymeric materials.
| Item Type: | Thesis (Bachelor's Thesis) |
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| Supervisor name: | Qian, C. |
| Degree programme: | Chemistry |
| Thesis type: | Bachelor's Thesis |
| Language: | English |
| Date Deposited: | 23 Jul 2025 06:51 |
| Last Modified: | 23 Jul 2025 06:51 |
| URI: | https://fse.studenttheses.ub.rug.nl/id/eprint/36458 |
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