A pH‐Gated Photocage
Source abstract
Abstract
Orthogonal control can be imposed on the photocleavage of a dioxinone heterocycle with the introduction of an amino substituent. Photoinduced electron transfer from this group to a naphthalene chromophore quenches the excited state responsible for the photochemical reaction. Protonation of the amino group prevents electron transfer and allows the cleavage of the dioxinone ring into a hydroxyester and a ketone.
Source: openalex_inverted_index · Quality: baseline
Research context
OpenAlex topics: Photochromic and Fluorescence Chemistry · Luminescence and Fluorescent Materials · Molecular Sensors and Ion Detection
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Laboratory for Molecular Photonics Department of Chemistry University of Miami 1301 Memorial Drive Coral Gables FL 33146‐0431 USA
Funding
National Science Foundation
References (29)
Show source-provided references
1. 10.1002/978352761824810.1002/9783527618248 ↗
2. 10.1016/j.tet.2005.05.04310.1016/j.tet.2005.05.043 ↗
3. 10.1039/C4CS00334A10.1039/C4CS00334A ↗
4. 10.1039/b912527m10.1039/b912527m ↗
5. 10.1021/cr900249z10.1021/cr900249z ↗
6. 10.1016/j.trac.2010.05.00510.1016/j.trac.2010.05.005 ↗
7. 10.1002/1521-4095(20020318)14:6<401::AID-ADMA401>3.0.CO;2-F10.1002/1521-4095(20020318)14:6<401::AID-ADMA401>3.0.CO;2-F ↗
8. 10.1002/cphc.20039000710.1002/cphc.200390007 ↗
9. 10.1038/nnano.2007.18810.1038/nnano.2007.188 ↗
10. 10.1002/asia.20100060310.1002/asia.201000603 ↗
11. 10.1039/B820280J10.1039/B820280J ↗
12. 10.1039/C4CS00342J10.1039/C4CS00342J ↗
13. 10.1002/anie.20046257710.1002/anie.200462577 ↗
14. 10.1021/ma060772110.1021/ma0607721 ↗
15. 10.1021/ma702364910.1021/ma7023649 ↗
16. 10.1021/ol070346f10.1021/ol070346f ↗
17. 10.1021/ol071085c10.1021/ol071085c ↗
18. 10.1021/jo800827510.1021/jo8008275 ↗
19. 10.1002/ejoc.20080096610.1002/ejoc.200800966 ↗
20. 10.1002/ejoc.20090009310.1002/ejoc.200900093 ↗
21. 10.1039/c2jm35173k10.1039/c2jm35173k ↗
22. 10.1002/978352763440810.1002/9783527634408 ↗
23. 10.1002/352760559210.1002/3527605592 ↗
24. The free‐energy change (ΔG°) for the electron‐transfer process was calculated with Equation () (G. J. Kavarnos Fundamentals of Photoinduced Electron Transfer VCH New York 1993). The oxidation potential (EOx) of the donor and the reduction potential (ERed) of the acceptor were determined from the cyclic voltammogram (Figure S12 Supporting Information) of 7. The energy change (ΔE00) for the S0→ S1transition of the naphthalene chromophore was estimated to be +3.50 eV from the absorption and emission spectra of 7. The donor–acceptor distance (d) was approximated to 0.6 nm.
25. 10.1021/ja512530810.1021/ja5125308 ↗
26. 10.1016/j.tetasy.2010.09.01010.1016/j.tetasy.2010.09.010 ↗
27. Berlman I. B. · 1971
28. 10.1007/978-0-387-46312-410.1007/978-0-387-46312-4 ↗
29. Scaiano J. C. · 1989