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In Situ Methylation Transforms Aggregation-Caused Quenching into Aggregation-Induced Emission: Functional Porous
Yehao Yan1, Richard M Laine2, Hongzhi Liu1
1Key Laboratory of Special Functional Aggregated Materials, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, P.R. China.
Abstract:
Methylation of TPA-DCM (2-(2,6-bis-4-(diphenylamino)stryryl-4H-pyranylidene)malononitrile) that exhibits aggregation-caused quenching (ACQ) results in the fluorophore M-TPA-DCM (2-(2,6-bis((E)-4-(di-p-tolylamino)-styryl)-4H-pyran-4-ylidene]malononitrile) that shows aggregation-induced emission (AIE) and NIR fluorescence and has a conjugated "D-π-A-π-D" electronic configuration. Friedel-Crafts reaction of TPA-DCM and octavinylsilsesquioxane (OVS) resulted in a family of porous materials (TPAIEs) that contain the M-TPA-DCM motif and show large Stokes shifts (180 nm), NIR emission (670 nm), tunable porosity (SBET from 160 to 720 m2 g-1 , pore volumes of 0.13-0.55 cm3 g-1 ), as well as high thermal stability (400 °C, 5 % mass loss, N2 ). As a simple test case, one of TPAIE materials was used to sense Ru3+ ions with high selectivity and sensitivity.
