Journal
CHEMISTRY OF MATERIALS
Volume 25, Issue 18, Pages 3718-3723Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cm402090k
Keywords
alkyne metathesis; organic porous materials; gas adsorption; dynamic covalent approach; poly(aryleneethynylene)
Funding
- National Science Foundation [IIP-1230142]
- American Chemical Society Petroleum Research Fund
- Directorate For Engineering
- Div Of Industrial Innovation & Partnersh [1034720, 1230142, 1034710] Funding Source: National Science Foundation
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The development of new synthetic methods has been a central challenge in the field of organic porous materials. Herein, we present the first application of alkyne metathesis to the synthesis of highly porous poly(aryleneethynylene) (PAE) networks. The permanent porosity of as-synthesized PAEs was confirmed by N-2 adsorption/desorption studies, and high Brunauer-Emmett-Teller (BET) specific surface areas (P/P-0 = 0.010.1) up to 2312 m(2).g(-1) were observed. PAE networks with the same chemical connectivity were also prepared through palladium-catalyzed Sonogashira cross-coupling under otherwise similar reaction conditions. The networks prepared through alkyne metathesis at three different temperatures (40 degrees C, 55 degrees C, and 75 degrees C) consistently exhibit a higher specific surface area and higher thermal stability, suggesting alkyne metathesis is advantageous in the preparation of highly porous organic materials. Our study demonstrates the feasibility of employing alkyne metathesis in the preparation of porous polymer networks and serves to expand the synthetic tool box for this emerging class of porous materials.
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