(Z)-Tetraphenylbut-2-ene-1, 4-diones: facile synthesis, tunable aggregation-induced emission and fluorescence acid sensing. Issue 13 (22nd March 2017)

• Record Type: Journal Article
• Authors: Li, Mengwei; Wang, Yi-Xuan; Wang, Jianhui; Chen, Yulan
• Is Part Of: Journal of materials chemistry. Volume 5:Issue 13(2017)
• Page Start: 3408
• Page End: 3414
• Publication Date: 2017-03-22
• Subjects: Materials -- Periodicals; Chemistry, Analytic -- Periodicals; Optical materials -- Research -- Periodicals; Electronics -- Materials -- Research -- Periodicals; 543.0284
• DOI: 10.1039/c7tc00173h
• Languages: English
• ISSNs: 2050-7526

Abstract

Abstract : A facile approach to synthesize stereospecific ( Z )-aryl-functionalized 1, 4-enediones has been presented. Abstract : A facile approach to synthesize stereospecific ( Z )-aryl-functionalized 1, 4-enediones has been presented. The resulting molecules (TPBD-1 andTPBD-2 ) were demonstrated as a new type of heteroatom-containing AIE-active luminogens with multiple sites for structural modifications. Knoevenagel reaction ofTPBD-1 led to a high electron affinity cyano derivative (TPBD-CN ), which showed enhanced AIE performance and pronounced red-emission. More interestingly, TPBD-1 exhibited acid-induced red emission both in dilute solution and in the solid state, which is attractive due to its great potential for turn-on optical sensing. The reversible fluorescence acid sensing can be attributed to the stepwise binding effect of carbonyl groups on the 1, 4-enedione core to rigidify the molecular conformation and strengthen the D–A interaction, which was systematically investigated by UV-vis, FL, FT-IR, and NMR spectroscopy and was further corroborated by DFT calculations.