Azobenzene photoswitches are {valuable|beneficial|useful|worthwhile|precious|important} tools for controlling properties of molecular systems with light. In {particular|specific|certain|distinct|unique}, {we have|we’ve|we’ve got} been investigating azobenzene glycoconjugates to probe carbohydrate-protein interactions {and also|as well as} to {design|style|design and style} photoresponsive glycomacrocycles with modulable chiroptical and physicochemical properties. To date, direct conjugation of glycosides to azobenzenes was performed by reactions {providing|supplying|offering|delivering|giving} target compounds in {limited|restricted} yields. We {therefore|consequently|as a result|for that reason|thus|hence} sought {for a|to get a|for any} {more|much more|a lot more|far more|additional|extra} {effective|efficient|successful|powerful|productive|helpful} and {reliable|dependable|trustworthy|reputable|trusted} coupling {method|technique|approach|strategy|system|process}. {In this|Within this} paper, we report on a {straightforward|simple} thioarylation of azobenzene derivatives with glycosyl thiols {as well|also|too|at the same time} as other thiol substrates, {increasing|growing|escalating|rising} the scope of azobenzene conjugation. Importantly, red-shifted azoswitches {that can be|that may be} addressed with visible light {were|had been|have been} {easily|effortlessly|very easily|simply|quickly|conveniently} functionalized and {challenging|difficult} unsymmetrical conjugates {were|had been|have been} {prepared|ready} in {good|great|excellent|very good|fantastic|superior} yields {via|by way of|through|by means of} sequential or {one|1|a single|one particular} pot procedures. {In addition|Additionally|Furthermore|Moreover|Also}, we took {advantage|benefit} {of the|from the|in the|on the|with the|of your} presence {of the|from the|in the|on the|with the|of your} sulfide bridge to tune {both|each} photochromic and thermal relaxation properties {of the|from the|in the|on the|with the|of your} core azobenzene {via|by way of|through|by means of} sulfur oxidation. {Based|Primarily based} on our photochemical investigations, we {finally|lastly|ultimately} demonstrated orthogonal three-state photoswitching in mixtures containing two distinct azobenzene thioglycosides. 1226898-93-6 Formula Formula of 1240587-88-5 PMID:23381601
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