Abstract
In this study, we report the synthesis of π-conjugated network polymers via palladium-catalyzed direct arylation polycondensation of triphenylamine (TPA) and tetraphenylethylene (TPE) with different active substrates. Moreover, six conjugated porous polymers were obtained (named as TPA-TPA-MA, TPA-PB-MA, TPA-TFB-MA, TPA-TPE-MA, TPE-PB-MA, and TPE-TFB-MA). Then, the fluorescence properties in the solid and dispersed states, the corresponding microporous structures, and the Brunauer–Emmett–Teller (BET) surface areas of all polymers were well studied. Among the obtained materials, TPA-PB-MA possessed not only largest BET surface area (686 m2 g−1) and largest pore volume (0.716 cm3 g−1), but also the smallest pore size of 0.823 nm. These properties are very beneficial for the application of TPA-PB-MA in CO2 storage and PA sensing. At 1 bar, TPA-PB-MA demonstrated the significant CO2 uptake of 2.70 and 1.35 mmol g−1 at 273 and 298 K, respectively. Furthermore, TPA-PB-MA was most sensitive and selective towards PA recognition. The KSV constant was measured as 4.0 × 104 M−1.
Highlights
The electron-de cient tails of methyl acrylate (MA) fully terminated the C–I bonds by the Heck cross-coupling reaction; this led to the formation of TPATPA-MA
MA was attached to TPA-TFB; this resulted in TPA-TFB-MA
A er washing several times with hot THF, sponge-like powders were produced; at rst, all of them were less emissive but porous in the solid phase. To enhance their emission performance and processability in organic solvents and their chemical stability due to the presence of atomic iodine, MA was fully terminated by the C–I bonds via the Heck crosscoupling reaction, leading to the corresponding polymers TPA-TPA-MA, TPA-phenylenebisboronic acid (PB)-MA, and TPA-TFB-MA (Scheme 1)
Summary
Conjugated polymers with a rigid framework are fascinating materials due to their extensive p-conjugation and the corresponding light-emitting behaviors.[1,2,3] conjugated porous polymers are more attractive because of their large surface areas, large capacity for gas storage, and interesting optical property for stimulus sensing;[4,5,6,7,8,9,10,11,12,13] certainly, the concept of aggregation-induced emission (AIE) has established a colorful emission platform for the optical science study.[14,15,16,17] In recent years, Tang's group has found that when AIEgens are incorporated into polymer networks, the polymer networks become able to partially interlock the free rotation of the embedded AIEgens.[18,19] As a result, molecular rotations can be restrained to some extent; this leads to more emissive polymers in the powder and in the solution state.[20,21] polymerization-promoted AIE systems have been designed and developed in recent years.[22,23,24,25]By integrating the desirable AIE feature with conjugated polymer characteristics, attractive materials could be generated.[26,27] Note that in conjugated polymer systems, the uorescent cores have multiple exciton transfer channels, which can lead to high sensitivity in the sensing processes by the expression of uorescence signals.[28,29] Due to the advantages of conjugated polymers, it is believed that the exploration of AIEactive conjugated polymers with their potential applications will be a hot research topic in the coming years.[30,31,32,33]. Synthesis of p-conjugated network polymers based on triphenylamine (TPA) and tetraphenylethylene (TPE) as building blocks via direct Pd-catalyzed reactions and their application in CO2 capture and explosive detection†
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