Azoarene photoswitches are versatile molecules that interconvert from their E-isomer to their Z-isomer with light. Azobenzene {is a|is really a|is actually a|can be a|is often a|is usually a} prototypical photoswitch but its derivatives {can be|may be|could be|might be|is often|is usually} poorly suited for in vivo applications {such as|like|including|for example|for instance|which include} photopharmacology {due to|because of|as a result of|on account of|resulting from|as a consequence of} undesired photochemical reactions promoted by ultraviolet light and its {relatively|fairly|comparatively|reasonably|somewhat} {short|brief|quick} half-life (t1/2) {of the|from the|in the|on the|with the|of your} Z-isomer ({2|two} days). Experimental and computational {studies|research} {suggest|recommend} that these properties (λmax {of the|from the|in the|on the|with the|of your} E isomer and t1/2 {of the|from the|in the|on the|with the|of your} Z-isomer) are inversely {related|associated|connected}. We identified isomeric azobisthiophenes and azobisfurans from a high-throughput screening study of 1700 azoarenes as photoswitch candidates with {improved|enhanced} λmax and t1/2 values relative to azobenzene. We {used|utilized|employed|utilised|applied|made use of} density functional theory to predict the activation {free|totally free|free of charge|cost-free|absolutely free|no cost} energies, reaction {free|totally free|free of charge|cost-free|absolutely free|no cost} energies, and vertical excitation energies {of the|from the|in the|on the|with the|of your} E- and Z-isomers of {2|two},2- and {3|three},3-substituted azobisthiophenes and azobisfurans. The half-lives {depend|rely} on {whether|whether or not|regardless of whether|no matter whether|no matter if|irrespective of whether} the heterocycles are 𝜋-conjugated or cross-conjugated {with the|using the|with all the|together with the} diazo 𝜋-bond. The {2|two},2-substituted azoarenes {both|each} have t1/2 values {on the|around the} scale of 1 hour, {while|whilst|although|even though|when|though} the {3|three},3-analogues have computed half-lives of 40 (thiophene) and 230 (furan) years. The {2|two},2-substituted heteroazoarenes have {significantly|considerably|substantially|drastically} {higher|greater|larger} λmax absorptions than their {3|three},3-substituted analogs: 76 nm for azofuran and 77 nm for azothiophene. Formula of (R)-JQ-1 (carboxylic acid) 6-Hydroxybenzo[d]thiazole-2-carbonitrile structure PMID:23290930
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