TY - JOUR A1 - Becker, Yvonne A1 - Roth, Sina A1 - Scheurer, Maximilian A1 - Jakob, Andreas A1 - Gacek, Daniel A. A1 - Walla, Peter Jomo A1 - Dreuw, Andreas A1 - Wachtveitl, Josef A1 - Heckel, Alexander T1 - Selective modification for red-shifted excitability: a small change in structure, a huge change in photochemistry T2 - Chemistry N2 - 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. KW - charge transfer KW - computational chemistry KW - fluorescence KW - photochemistry KW - photolabile protecting groups Y1 - 2020 UR - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/63855 UR - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-638559 SN - 1521-3765 N1 - Open access funding enabled and organized by Projekt DEAL. VL - 27 IS - 6 SP - 2212 EP - 2218 PB - Wiley-VCH CY - Weinheim ER -