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Exploration of Thiazolo[5,4‐ d ]thiazole Linkages in Conjugated Porous Organic Polymers for Chemoselective Molecular Sieving
Author(s) -
Biswal Bishnu P.,
Becker Daniel,
Chandrasekhar Naisa,
Seenath Jensheer Shamsudeen,
Paasch Silvia,
Machill Susanne,
Hennersdorf Felix,
Brunner Eike,
Weigand Jan J.,
Berger Reinhard,
Feng Xinliang
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802631
Subject(s) - moiety , porosity , polymer , thiazole , aqueous solution , adsorption , chemoselectivity , chemical engineering , conjugated system , materials science , chemistry , polymer chemistry , organic chemistry , combinatorial chemistry , catalysis , engineering
Porous organic polymers (POPs) have attracted significant attention towards molecular adsorption in recent years due to their high porosity, diverse functionality and excellent chemical stability. In this work, we present a systematic case study on the formation of thiazolo[5,4‐ d ]thiazole (TzTz) linkages through model compounds and its integration to synthesize a set of three novel, thermo‐chemically stable TzTz‐linked POPs, namely TzTz‐POP‐3 , TzTz‐POP‐4 , and TzTz‐POP‐5 with triphenylbenzene, tetraphenylpyrene and tetra(hydroxyphenyl)methane cores, respectively. Interestingly, the integrated TzTz moiety of the represented TzTz‐POP‐3 renders chemoselective removal of organic dye fluorescein (FL) from a mixture with parafuchsine (FU) in aqueous solution. The TzTz‐POP‐3 offered excellent chemoselectivity of ≈1:7 (FL:FU), compared to alike porous materials demonstrated for similar applications due to the presence of multiple active anchoring sites coupled with permanent porosity and appropriate pore window.