Odd-Even Alternation in Tautomeric Porous Organic Cages with Exceptional Chemical Stability

Bera, Saibal ; Basu, Arghya ; Tothadi, Srinu ; Garai, Bikash ; Banerjee, Subhrashis ; Vanka, Kumar ; Banerjee, Rahul (2017) Odd-Even Alternation in Tautomeric Porous Organic Cages with Exceptional Chemical Stability Angewandte Chemie International Edition, 56 (8). pp. 2123-2126. ISSN 1433-7851

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Official URL: http://doi.org/10.1002/anie.201611260

Related URL: http://dx.doi.org/10.1002/anie.201611260

Abstract

Amine‐linked (C−NH) porous organic cages (POCs) are preferred over the imine‐linked (C=N) POCs owing to their enhanced chemical stability. In general, amine‐linked cages, obtained by the reduction of corresponding imines, are not shape‐persistent in the crystalline form. Moreover, they require multistep synthesis. Herein, a one‐pot synthesis of four new amine‐linked organic cages by the reaction of 1,3,5‐triformylphloroglucinol (Tp) with different analogues of alkanediamine is reported. The POCs resulting from the odd diamine (having an odd number of −CH2 groups) is conformationally eclipsed, while the POCs constructed from even diamines adopt a gauche conformation. This odd–even alternation in the conformation of POCs has been supported by computational calculations. The synthetic strategy hinges on the concept of Schiff base condensation reaction followed by keto–enol tautomerization. This mechanism is the key for the exceptional chemical stability of cages and facilitates their resistance towards acids and bases.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc..
Keywords:Chemical Stability; Keto–Enol Tautomerism; Odd–Even Effect; Porous Organic Cages.
ID Code:115753
Deposited On:16 Mar 2021 08:00
Last Modified:16 Mar 2021 08:00

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