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Published on: June 25, 2018
Pillarureaarenes: Urea-Embedded Pillararenes for Amino Acid Derivative Recognition
Kai Diao1, Wang Xie1, Mingyue Wen1
1State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
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A three-dimensional pillarureaarene (P3U6A) was synthesized via fragment-coupling cyclization of dialkoxybenzene and urea units. Single-crystal analysis revealed a shield-shaped structure stabilized by intramolecular hydrogen bonds. The macrocycle demonstrated strong binding with phenylalanine ethyl ester salts. Further derivatization gave P3EU6A, showing chiral recognition of a series of amino acid derivatives via induced circular dichroism (CD). This work introduces a versatile platform for constructing urea-embedded pillararenes with potential applications in host-guest chemistry and chirality sensing.
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The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

