Issue 10, 2017

2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2-b]pyrrole (AAPP) AIEgens: tunable RIR and TICT characteristics and their multifunctional applications

Abstract

Aggregation-induced emission luminogens (AIEgens) have attracted extensive interest for their outstanding luminescence properties in the aggregated state and even in the solid state. In this work, we developed a series of novel AIEgens based on 2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2-b]pyrrole (AAPP). The AIEgens can be facilely synthesized through a single-step reaction under mild conditions with satisfactory yields. Interestingly, AAPP was found to have multiple luminous mechanisms that result in variable fluorescence properties. The propeller-like structure of AAPP enables a restricted intramolecular rotation (RIR) process which significantly enhances its fluorescence in the aggregated state (i.e. AIE fluorescence). In addition, there is a donor–acceptor interaction between the heterocycle center and the alkoxycarbonyl units in AAPP which allows a typical twisted intramolecular charge transfer (TICT) process in the dispersed state, resulting in strong fluorescence emissions in non-polar or low-polarity solvents but fluorescence quenching in high-polarity solvents. Due to the tunable RIR and TICT processes and the multiple fluorescence, AAPP compounds exhibit multifunctional applications: (1) as a reversible fluorescent thermometer, AAPP exhibited excellent fatigue resistance. There was a good linear relationship between its fluorescence intensity and temperature from 10 °C to 60 °C. (2) The desethyl AAPP derivative (CAPP) was successfully applied in the detection of Cd(II) in aqueous solution at neutral pH, and showed a 500-fold fluorescence “turn-on” response to Cd(II) with good selectivity.

Graphical abstract: 2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2-b]pyrrole (AAPP) AIEgens: tunable RIR and TICT characteristics and their multifunctional applications

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Jul 2017
Accepted
31 Aug 2017
First published
31 Aug 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 7258-7267

2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2-b]pyrrole (AAPP) AIEgens: tunable RIR and TICT characteristics and their multifunctional applications

K. Li, Y. Liu, Y. Li, Q. Feng, H. Hou and B. Z. Tang, Chem. Sci., 2017, 8, 7258 DOI: 10.1039/C7SC03076B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements