Organic Fluorescent Compounds that Display Efficient Aggregation-Induced Emission Enhancement and Intramolecular Charge Transfer.

Ruibin Hou,Yan Xia,Dongfeng Li,Baohua Zhao

doi:10.3390/molecules23061446

Ruibin Hou, Yan Xia + Show 2 more

Open Access

https://doi.org/10.3390/molecules23061446

Copy DOI

Abstract

A series of symmetric sulfone-linked organic fluorescent compounds (1a–c) was synthesized and characterized. V-shaped 1a–c were designed as aggregate of intramolecular charge transfer (ICT) and aggregation-induced emission enhancement (AIEE) processes. The 1a–c emitted intense blue violet lights in normal solvents. A large red shift of the emission wavelength and dramatic decrease of emission efficiency occurred with increasing solvent polarity. The 1a–c will function well as electron transport and blue light-emitting materials through theoretical calculations.

Highlights

Fluorescent organic molecules are widely used as active elements in organic light-emitting diodes (OLED), chemosensors, and bioprobes [1,2,3,4,5]
Propeller-shaped molecules such as hexaphenylsilole, tetraphenylethene, and quinoline-malononitrile and their derivatives are known for their unique ability to promote aggregation-induced emission (AIE) [12]
The solvent polarity influences the AIE effect. These data illustrate our speculation that 1a is a luminogen with both intramolecular charge transfer (ICT) and AIE characteristics

Summary

Introduction

Fluorescent organic molecules are widely used as active elements in organic light-emitting diodes (OLED), chemosensors, and bioprobes [1,2,3,4,5]. Most of these fluorescent organic molecules possess planar conjugated structures and display reasonable emission in dilute solutions, their emission is weak or nonexistent in the solid state because of aggregation-caused quenching. Such quenching limits the applications of fluorescent organic molecules [6,7,8]. The integration of AIE and intramolecular charge transfer (ICT) into one molecule has attracted much attention This type of luminophore can emit strong fluorescence in the aggregated form or solid state and in dilute solution [13,14,15].

Synthesis of Target Compounds 1a–c

The Optical Properties of Compounds 1a–c

The Electrochemical Properties of 1a–c

Theoretical Calculations

Experimental

Conclusions