Selective modification for red-shifted excitability: a small change in structure, a huge change in photochemistry
- We developed three bathochromic, green-light activatable, photolabile protecting groups based on a nitrodibenzofuran (NDBF) core with D-π-A push–pull structures. Variation of donor substituents (D) at the favored ring position enabled us to observe their impact on the photolysis quantum yields. Comparing our new azetidinyl-NDBF (Az-NDBF) photolabile protecting group with our earlier published DMA-NDBF, we obtained insight into its excitation-specific photochemistry. While the “two-photon-only” cage DMA-NDBF was inert against one-photon excitation (1PE) in the visible spectral range, we were able to efficiently release glutamic acid from azetidinyl-NDBF with irradiation at 420 and 530 nm. Thus, a minimal change (a cyclization adding only one carbon atom) resulted in a drastically changed photochemical behavior, which enables photolysis in the green part of the spectrum.
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| Author: | Yvonne Becker, Sina Roth, Maximilian Scheurer, Andreas Jakob, Daniel A. Gacek, Peter Jomo Walla, Andreas DreuwORCiDGND, Josef WachtveitlORCiDGND, Alexander HeckelORCiDGND |
|---|---|
| URN: | urn:nbn:de:hebis:30:3-638559 |
| DOI: | https://doi.org/10.1002/chem.202003672 |
| ISSN: | 1521-3765 |
| Parent Title (English): | Chemistry |
| Publisher: | Wiley-VCH |
| Place of publication: | Weinheim |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2020/09/21 |
| Date of first Publication: | 2020/09/21 |
| Publishing Institution: | Universitätsbibliothek Johann Christian Senckenberg |
| Release Date: | 2022/03/15 |
| Tag: | charge transfer; computational chemistry; fluorescence; photochemistry; photolabile protecting groups |
| Volume: | 27 |
| Issue: | 6 |
| Page Number: | 7 |
| First Page: | 2212 |
| Last Page: | 2218 |
| Note: | Open access funding enabled and organized by Projekt DEAL. |
| HeBIS-PPN: | 493479961 |
| Institutes: | Biochemie, Chemie und Pharmazie |
| Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Sammlungen: | Universitätspublikationen |
| Licence (German): |  Creative Commons - Namensnennung 4.0 |
