Zn(ii) phthalocyanines tetra substituted by aryl and alkyl azides: design, synthesis and optical detection of H₂S

Abstract

Experimental examination of two novel Zn(ii)-phthalocyanines having aryl and alkyl azide functional groups at the peripheral positions that have been designed/synthesized for hydrogen sulfide (H2S) sensing purposes.

Synthesis and formulation of self‐immolative PEG‐aryl azide block copolymers and click‐to‐release reactivity with trans‐cyclooctene

“…The AzNPs were incubated with GSH at expected biological concentrations (5 mM) and limited‐to‐no decrease in the azide peak was observed. This supported the previous literature where aryl azides were unreactive toward GSH 44,45 suggesting that our reported aryl azide NPs have an advantage over their alkyl azide counterparts in that they can be activated by TCO in the presence of GSH.…”

“…While the structure of the aryl azide dictates its reactivity, [33][34][35] functionalised aryl azides have relatively high biological stability, with selective reactivity for strained alkenes and alkynes ([3+2]-cycloadditions), [35][36][37] triphenylphosphines (Staudinger reaction), 38 or H 2 S. [39][40][41] We have developed the alkene-azide [3+2]-cycloaddition as a bioorthogonal click-to-release reaction for prodrugs 28,29,32 and hydrogels, 30,31 while others have investigated H 2 S; a gaseous transmitter in the body, as an activation mechanism for aryl azide-containing probes, prodrugs, and materials. [39][40][41] Alkyl azides can also be reduced by H 2 S 42 or glutathione, 43 however, aryl azides are considered more responsive to, and selective toward, alkenes and H 2 S, 44 even in the presence of other endogenous thiol/thiolate species (e.g., glutathione). 45 Examples of alkyl azide block copolymers used in polymeric drug delivery systems have been reported by Yan 42 and Stang, 43 whereby the alkyl azide is reduced by H 2 S and glutathione, respectively.…”

Effects of anchoring and spacer groups of asymmetric zinc phthalocyanines on the photovoltaic performance of dye-sensitized solar cells

“…3a and b). 32,33 The characteristic molecular ion peaks of compounds 3, 6, and 7 were observed at m/z: 394.…”

Azide Thermolysis Frameworks: Self‐inflating, Porous, and Lightweight Materials

“…Supporting Information is available from the Wiley Online Library or the author. Additional references are cited within the Supporting Information [12–18] …”