Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 8, Pages 2123-2126Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611260
Keywords
chemical stability; keto-enol tautomerism; odd-even effect; porous organic cages
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Funding
- CSIR, India
- CSIR, India [YSS/2015/000606]
- CSIR [CSC0122, CSC0102]
- DST [SB/S1/IC-32/2013INT/SIN/P-05SR/NM/NS-1179/2012G]
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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, aminelinked 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.
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