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.
Author:Yvonne Becker, Sina Roth, Maximilian Scheurer, Andreas Jakob, Daniel A. Gacek, Peter Jomo Walla, Andreas DreuwORCiDGND, Josef WachtveitlORCiDGND, Alexander HeckelORCiDGND
Parent Title (English):Chemistry
Place of publication:Weinheim
Document Type:Article
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
Page Number:7
First Page:2212
Last Page:2218
Open access funding enabled and organized by Projekt DEAL.
Institutes:Biochemie, Chemie und Pharmazie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoCreative Commons - Namensnennung 4.0