Synthesis of anthracene zinc (II) cyclen complex for recognition of carbamazepine

Junaidi, Sofiah (2016) Synthesis of anthracene zinc (II) cyclen complex for recognition of carbamazepine. [Student Project]
Abstract

9, 10-Bis( 1,4, 7, 10-tetraazacyclododecane-1-ylmethyl)anthracene or anthracene zn2+­ cyclen complex is synthesized through three step chemical reaction as a complex compound that will form π-π stacking with carbamazepine. The aim of the study was to evaluate the π-π interaction between anthracene Zn2+-cyclen complex with carbamazepine through fluorescence intensity. The fluorescence activity will be assessed using fluorescence spectrometer. The first step was protection of cyclen with ditertbutyl di carbonate forming 1,4, 7-tris(tertbutyloxycarbonyl)-1,4, 7, 10-tetraazacyclododecane. The second step was formation of 9,10-bis(3Boc-cyclen)anthracene by reacting 3Boc­ cyclen with 9, 10-bis(bromomethyl)anthracene. The last step was deprotection of 9, 1 O­ bis(3Boc-cyclen)anthracene with concentrated HBr and MeOH to form anthracene zn2+­ cyclen complex. Then, the anthracene Zn2+-cyclen complex and carbamazepine will be placed in aqueous condition to allow π-π interaction. However, identification by TLC and confirmation by 1H NMR spectroscopy of the last step does not show desired outcome. The deprotection of 9,10-bis(3Boc-cyclen)anthracene to form 9,10-Bis(1,4,7,10- tetraazacyclododecane-1-ylmethyl)anthracene was unsuccessful. Thus, the study cannot be proceed until evaluation of fluorescence intensity to demonstrate interaction between carbamazepine and anthracene Zn2+-cyclen complex. Yet, there are still possibilities of anthracene Zn2+-cyclen complex usage for recognition of carbamazepine.

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