TY - JOUR
T1 - Construction of crystalline 2D covalent organic frameworks with remarkable chemical (Acid/Base) stability via a combined reversible and irreversible route
AU - Kandambeth, Sharath
AU - Mallick, Arijit
AU - Lukose, Binit
AU - Mane, Manoj V.
AU - Heine, Thomas
AU - Banerjee, Rahul
PY - 2012/12/5
Y1 - 2012/12/5
N2 - 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.
AB - 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.
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U2 - 10.1021/ja308278w
DO - 10.1021/ja308278w
M3 - Article
C2 - 23153356
AN - SCOPUS:84870659680
SN - 0002-7863
VL - 134
SP - 19524
EP - 19527
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 48
ER -