The regioselective poly-functionalization of {highly|extremely|very|hugely} symmetric spherical Ih-C60 is {extremely|very|incredibly|really|particularly|exceptionally} {challenging|difficult} and {usually|generally|typically|normally|commonly|ordinarily} {leads to|results in} the formation of regio-isomeric mixtures not amenable for HPLC purification. {Recently|Lately|Not too long ago}, {we have|we’ve|we’ve got} pioneered the regioselective functionalization of C60 fullerene {under|below|beneath} a supramolecular mask {strategy|technique|method|approach|tactic}, {using|utilizing|making use of|employing|working with|applying} tetragonal prismatic nanocapsules to encapsulate C60 and performing the Bingel tetrakis-cyclopropanation {at the|in the} exposed fullerene surface {through|via|by means of|by way of} the {four|4} windows {of the|from the|in the|on the|with the|of your} nanocapsule. {Here|Right here}, we describe an extension {of the|from the|in the|on the|with the|of your} supramolecular mask {strategy|technique|method|approach|tactic} for the selective Diels-Alder (DA) functionalization of Ih-C60 {using|utilizing|making use of|employing|working with|applying} acenes. The supramolecular mask {allows|enables|permits|makes it possible for} the chemo- and regioselective synthesis of e,e-bis-anthracene-C60 (functionalization at 90o) or the synthesis of trans-1-bis-pentacene-C60 (functionalization at 180o), only by {changing|altering} the acene length. {Moreover|Furthermore|In addition|Additionally}, the mask {strategy|technique|method|approach|tactic} {allows|enables|permits|makes it possible for} to {obtain|acquire|get|receive} unprecedented equatorial hetero-tris-functionalized-C60 adducts combining Diels-Alder with Bingel mask regiofunctionalization. Computational modelling revealed {significant|substantial|considerable|important} {differences|variations} {in the|within the|inside the} host-guest interactions and equilibrium established {between|in between|among|amongst|involving} the firstly formed anthracene- and pentacene-based monoadducts {with the|using the|with all the|together with the} nanocapsule, respectively, which {finally|lastly|ultimately} {determine|figure out|decide|establish|ascertain|identify} the observed orthogonal regioselectivity. The {combination|mixture} of Molecular Dynamics (MD) simulations and {analysis|evaluation} of Frontier Molecular Orbital (FMO) involved {in the|within the|inside the} Diels-Alder cycloadditions {provide|offer|supply|give|present|deliver} {crucial|essential|vital|critical|important} insights to rationalize the regioselective {control|manage|handle} exerted by the supramolecular mask. Buy913820-87-8 408492-27-3 supplier PMID:24189672
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