Exploration of Thiazolo[5,4-d]thiazole Linkages in Conjugated Porous Organic Polymers for Chemoselective Molecular Sieving

Bishnu P Biswal; Daniel Becker; Naisa Chandrasekhar; Jensheer Shamsudeen Seenath; Silvia Paasch; Susanne Machill; Felix Hennersdorf; Eike Brunner; Jan J Weigand; Reinhard Berger; Xinliang Feng

doi:10.1002/chem.201802631

Exploration of Thiazolo[5,4-d]thiazole Linkages in Conjugated Porous Organic Polymers for Chemoselective Molecular Sieving

Chemistry. 2018 Jul 25;24(42):10868-10875. doi: 10.1002/chem.201802631. Epub 2018 Jun 28.

Affiliations

¹ Faculty of Chemistry and Food Chemistry, Center for Advancing Electronics Dresden, Technische Universitat Dresden, 01062, Dresden, Germany.
² Chair of Bioanalytical Chemistry, Technische Universität Dresden, 01062, Dresden, Germany.
³ Chair of Inorganic Molecular Chemistry, Technische Universität Dresden, 01062, Dresden, Germany.

PMID: 29808944
DOI: 10.1002/chem.201802631

Abstract

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.

Keywords: microporous materials; molecular sieves; porous organic polymers; thiazolo[5,4-d]thiazole; water treatment.