Synthesis And Fluorescent Properties Of Pyrrole Derivatives With(4-hydroxymethyl-phenyl)acetenyl

Searching for the relationship between the emission wavelength and chemical structure are theoretical foundations for designing and synthesizing long emission wavelength compounds. Increasing conjugated degree or projecting linear donor-acceptor structure are effective ways in order to adjust the fluorescent emission wavelength of compounds. But the aggregation-caused quenching phenomenon is ubiquitous among the luminescent compounds, this phenomenon limited the application of luminescent compounds in the field of long-time bioimaging. Through molecular structure design and optimization, the discovery and development of aggregation-induced emission compounds could commendably solve this problem. Comparing to the traditional fluorescent compounds, aggregation-induced emission or aggregation-induced emission enhance materials have more outstanding advantages in chemical sensing, anti-photobleaching, bioprobe area, and so on. For instance, they could be used for turn-on chemical probe, anti-photobleaching biological probe, et al.Three categories of pyrrole derivatives which containing electron donor(pyrrole) and electron acceptor(methyl formate) structure have been synthesized in this paper, the donor and acceptor are linked conjugately by acetenyl group. MB3(T shape), MB3PE2(T-Ï€ shape) and MB5(five-star shape) have been successfully synthesized by designing the donor-acceptor geometry, and the structures of these compounds have already been comfirmed by NMR, MS, and at al. After carefully studied the luminance of these three compounds in the aggregation state, we found that the geometric construction has significant influence on their emission wavelength and intensity. Through the methods of quantum chemical calculation, quantum yield and fluorescent lifetime, we discussed the relationship between the geometry and their emissive properties. We found that five-star shape compound MB5 is insensitive to the solvent polarity and has the longer emission wavelength. In addition, it can specifically recognize the cell membrane of some cells. It is one kind of potential dyes which could emit red fluorescence for the cell membrane imaging.