Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route
Sharath Kandambeth, Arijit Mallick, Binit Lukose, Manoj V. Mane, Thomas Heine, Rahul Banerjee*
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引用次数: 1109
Abstract
Two new chemically stable [acid and base] 2D crystalline covalent organic frameworks (COFs) (TpPa-1 and TpPa-2) were synthesized using combined reversible and irreversible organic reactions. Syntheses of these COFs were done by the Schiff base reactions of 1,3,5-triformylphloroglucinol (Tp) with p-phenylenediamine (Pa-1) and 2,5-dimethyl-p-phenylenediamine (Pa-2), respectively, in 1:1 mesitylene/dioxane. The expected enol–imine (OH) form underwent irreversible proton tautomerism, and only the keto–enamine form was observed. Because of the irreversible nature of the total reaction and the absence of an imine bond in the system, TpPa-1 and TpPa-2 showed strong resistance toward acid (9 N HCl) and boiling water. Moreover, TpPa-2 showed exceptional stability in base (9 N NaOH) as well.
采用可逆和不可逆有机联合反应合成了两种新的化学稳定的[酸和碱]二维结晶共价有机骨架(TpPa-1和TpPa-2)。以1,3,5-三甲酰基间苯三酚(Tp)与对苯二胺(Pa-1)和2,5-二甲基-对苯二胺(Pa-2)为基料，以1:1的三甲苯/二恶烷为溶剂，进行席夫碱反应合成了这些COFs。预期的烯醇-亚胺(OH)形式发生了不可逆的质子互变异构，只观察到酮-烯胺形式。由于整个反应的不可逆性质和体系中不存在亚胺键，TpPa-1和TpPa-2对酸(9 N HCl)和沸水具有较强的抗性。此外，TpPa-2在碱(9 N NaOH)中也表现出优异的稳定性。
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