We {develop|create} {the first|the very first|the initial} {method|technique|approach|strategy|system|process} for catalytic, exhaustive ortho-alkoxylation of azobenzene photoswitches. Alkoxylation is {known|recognized|identified} {to improve|to enhance} the photoswitch properties that {control|manage|handle} azobenzenes’ {success|achievement|good results|accomplishment|results} in chemical biology or {materials|supplies|components} sciences: e.g. {better|much better|far better|greater|superior|improved} completeness of {both|each} E→Z and Z→E photoisomerisations, and >100 nm red-shifting of photoresponse. PMID:23773119 (DHQD)2AQN Chemscene Buy279236-77-0 Our {method|technique|approach|strategy|system|process} enables {straightforward|simple} late-stage diversification of photoswitches with {interesting|fascinating|intriguing|exciting} functional handles. We showcase {four|4} applications, {using|utilizing|making use of|employing|working with|applying} it to rationally tune lipophilicity, prepare isotopic tracers for metabolism {studies|research}, {install|set up} {full|complete} water solubility {without|with out|without having|with no|devoid of|without the need of} ionic charges, and {efficiently|effectively} access previously {difficult|tough|challenging|hard|tricky|complicated} mixed-substituent photoswitches. We also identified a previously unstudied mixed-substituent tetra-ortho-family, difluoro-dialkoxy-azobenzenes, whose photoresponse can outperform {previous|prior|earlier|preceding} ‘gold standard’ tetrafluoro-, dichloro-difluoro-, and tetrachloro-azobenzenes in {significant|substantial|considerable|important} {ways|methods|techniques|approaches|strategies}. We {thus|therefore|hence|as a result} {expect|anticipate|count on} that {both|each} the scaffolds we showcase {and the|and also the|as well as the|along with the|plus the} {method|technique|approach|strategy|system|process} we {develop|create} will {impact|influence|effect} broadly on photochemistry and photopharmacology.
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