Long‐Wavelength Photolysis of Amino Acid 6‐(Methoxy‐2‐oxo‐2H‐naphtho[1,2‐b]pyran‐4‐yl)methyl Esters

Abstract

(6-Methoxy-2-oxo-2H-naphtho[1,2-b]pyran-4-yl)methyl esters of valine or phenylalanine as model bifunctional molecules were synthesised to assess its applicability as a photocleavable protecting group for solution phase organic synthesis and in caging applications at longer wavelengths. The behaviour of the corresponding derivatives towards photoly-

Photoactivable heterocyclic cages in a comparative release study of butyric acid as a model drug

“…This is indicative of the presence of different excited state species and the outcome of these measurements is presented in Table 3. The behaviour seen is in keeping with our previous observations [19,20,26] and the longer-lived emission can relate to unquenched (potentially cleaved) fluorophore. The shorter-lived decays are attributed to charge transfer states, caused by the presence of the conjugate upon excitation, with the possibility of the formation of an ion pair that can either recombine or progress to a cleaved pair.…”

“…Considering the know-how of the authors in the field of fluorescent photoactivable molecules based on aromatic and heteroaromatic skeletons for the release of bioanalytes [17][18][19][20][21][22][23][24], in connection with the interest in the development of alternative light sensitive prodrugs, and following the previous work regarding butyric acid, a new set of oxygen and nitrogen heterocyclic cages were synthesised. The use of these heterocyclic moieties can result in longer maximum wavelengths of absorption, allowing the photorelease of butyric acid at longer wavelengths, not detrimental to bioapplications.…”

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

“…Benzocoumarin derivatives typically have similar or slightly hypsochromically shifted absorption maxima relative to 4-methyl­coumarin ,, (λ max abs = 274–321 nm vs 310 nm), but their spectroscopic properties can be modified by introducing EDGs or EWGs to modulate their ICT states . Gonçalves, Costa, and co-workers reported on several benzocoumarin PPGs ( 63 – 68 ); their structures and photophysical and photochemical properties relating to the photorelease of various carboxylic acids are shown in Table . ,− …”

Base-Promoted Selective Synthesis of 2H-Pyranones and Tetrahydronaphthalenes via Domino Reactions

“…In addition, the small polycyclic aromatic hydrocarbon fluorophores and small biconjugated linear and nonlinear aromatic molecules with built-in donor–acceptor (D–A) architectures have amazing applications in electroluminescent (EL) materials. 5…”

“…In common, the structural features of small organic functional chromophores embedded within N-, O-, and S-atom-containing fluorophores are particularly used in organic light emitting diodes (OLEDs), liquid crystal displays (LCDs) of mobile phones, fluorescent dyes, and highly effective sensor and biological probes. In addition, the small polycyclic aromatic hydrocarbon fluorophores and small biconjugated linear and nonlinear aromatic molecules with built-in donor–acceptor (D–A) architectures have amazing applications in electroluminescent (EL) materials …”