Design, Synthesis And Properties Of Novel Luminescent Molecules Induced By Quinodiphthol

Fluorescent materials, especially those with advanced properties, are of great importance due to their widespread applications in the fields of optoelectronic devices, environmental sensors, and biological science. However, most of the traditional fluorophores suffer from aggregation-induced-quenching (ACQ) effect, which prevent their applications in solid or aggregated state. In 2001, Tang's group firstly discovered an intriguing aggregation-induced emission (AIE) phenomenon. Binaphthol (BINOL), a well-known versatile chiral fluorophore, attracts great interest due to its structural diversity and excellent luminescence, and provides a widespread application in optical-based molecular detection. However, BINOL suffers from a notorious ACQ effect, limiting its practical application in some fields. In recent years, to overcome this undesirable nature, scientists obtained AIE molecules attaching typical AIE unit-tetraphenylethene (TPE) to BINOL moieties. Despite these elegant examples, a straightforward protocol to generate chiral AIE-active BINOL derivatives remains a long-standin challenge.Metal ions play an important role to obtain physiological function and metabolism. Copper ion, the third most abundant transition metal ion in the body, plays a crucial role in numerous enzyme functions. The incorrect regulation of Copper ion always related to a series of diseases, such as Alzheimer's, Parkinson's and Wilson's diseases. As a result, researchers pay more attention to the dection of Copper ion.In order to change the nature of BINOL and synthesized chiral AIE-active BINOL derivatives, which can be served as ion fluorescence sensor. The paper performed the following work:(1) In this paper, we designed and synthesized a series of chiral AIE-active BINOL derivatives, and show abnormally high aggregation induced CD signal quenching phenomenon. The intermediates and target products were characterized by NMR, mass spectrometry and fluorescence. The work provides a simple and powerful method to build a chiral AIE system based on the BINOL backbone and opens up new perspectives for the construction of chiral fluorescent sensors.(2) In this paper, we synthesized a novel BINOL-based fluorescence sensor (BINOP-CN), which shows higher selectivity towards Copper ion without any interference of other ions. In addition, the complex was observed by X-ray crystal lography.SEM images reveal that BINOP-CN can form nano-polyhedra in the aggregate state, but self-assemble into micro-branches after adding Copper ion.