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Picric acid sensing and \(\hbox {CO}_{2}\) capture by a sterically encumbered azo-linked fluorescent triphenylbenzene based covalent organic polymer


A sterically encumbered isopropyl group substituted fluorescent triphenylbenzene based azo-linked covalent organic polymer, \(^{i}\)PrTAPB-Azo-COP, has been synthesized by Cu(I) catalysed homo coupling (amine-amine) reaction of 1,3,5-tris(\(4'\)-amino-\(3',5'\)-isopropylphenyl)benzene (\(^{i}\)PrTAPB) under aerobic conditions. The Brunauer-Emmett-Teller (BET) and Langmuir surface areas of \(^{i}\)PrTAPB-Azo-COP have been estimated to be 395 and 697 \(\hbox {m}^{2}\) g\(^{-1}\) with a pore diameter of 11.6 Å. Due to the presence of fluorescent triphenylbenzene platform \(^{i}\)PrTAPB-Azo-COP exhibits broad emission band centred at 428 nm, when excited at 300 nm, as a result of extended conjugation. The inherent fluorescent nature of \(^{i}\)PrTAPB-Azo-COP has been utilized for sensing electron-deficient polynitroaromatic compounds (PNACs) such as a picric acid (PA), dinitrotoluene (DNT), p-dinitrobenzene (p-DNB) and m-dinitrobenzene (m-DNB). Further, \(^{i}\)PrTAPB-Azo-COP has also been utilized for capture of carbon dioxide as the azo-COP is enriched with \(\hbox {CO}_{2}\)-philic nitrogen atoms apart from its microporosity. Since the azo (–N=N-) linkages are masked by the bulky isopropyl groups, \(^{i}\)PrTAPB-Azo-COP exhibits a \(\hbox {CO}_{2}\) uptake of 6.5 and 19.4 wt% at 1 bar and 30 bar, respectively, at 273 K.

Graphical Abstract

SYNOPSIS Sterically encumbered azo-linked covalent organic polymer (\(^{i}\)PrTAPB-Azo-COP) has been synthesized from a fluorescent hexaisopropyl substituted triphenylbenzene platform. The resulting fluorescent porous COP has been utilized for picric acid sensing and \(\hbox {CO}_{2}\) capture.

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This work was supported by SERB, New Delhi (SB/S1/IC-48/2013) and IIT-Bombay Bridge Funding. R. M. thanks, SERB, New Delhi for J. C. Bose Fellowship (SB/S2/JCB-85/2014). D. K. thanks UGC, New Delhi, for a research fellowship.

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Kaleeswaran, D., Murugavel, R. Picric acid sensing and \(\hbox {CO}_{2}\) capture by a sterically encumbered azo-linked fluorescent triphenylbenzene based covalent organic polymer. J Chem Sci 130, 1 (2018).

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  • Azo linkage
  • COPs
  • \(\hbox {CO}_{2}\) capture
  • nitroaromatic sensing
  • triphenylbenzene