The control of ultrafast reversible reaction of BODIPY chromophore and its application in fluorescence detection

Boron atom has a strong electron deficient property because of its empty P orbit When boron atom is combined with π electron system, it can form a π - conjugated system containing boron with special intramolecular charge transfer property, and then show a series of very special photophysical and photochemical properties Among them, the boron atoms can be hybridized by SP 2 to form the three coordinated organic boron compounds, or the four coordinated organic boron compounds can be hybridized by SP 3 In recent years, researchers in the Key Laboratory of photochemistry, Institute of chemistry, Chinese Academy of sciences have been devoted to the study of boron-containing organic compounds, and proposed the luminescence mechanism of the specific fluorescence properties of triarylbroms (angelw Chem Int ed 2011, 50, 8072-8076; chem Commun 2014, 50, 2778-2780;), a series of special supramolecular structure fluorescent probes were designed and prepared, which were used to detect the changes of temperature, pH and other micro environments in cells and organisms and the fluorescence of multiple active species (angelw Chem Int ed 2014, 53, 7809-7813; anal Chem 2015, 87, 3694-3698; anal Chim Acta 2015, 869, 81-88; anal Chem 2016, 88 , 1052-1057）。
Figure a: mechanism and schematic diagram of base induced meso site unsubstituted BODIPY dimerization; figure B: spectral response of BODIPY dimerization system to formaldehyde (b); figure C and D: fluorescence response of BODIPY dimerization system to temperature Source: Recently, with the support of NSFC, the Ministry of science and technology and the Chinese Academy of Sciences, Yang Guoqiang's research group adopted the no substitute BODIPY 2, The selective modification of 6-substituents, for the first time, realized the rapid and reversible dimerization of BODIPY induced by alkali The strong luminescent properties of BODIPY were quenched due to the change of conjugated structure of dimers When the species which can react with the inducer alkali was encountered, the dimers could dissociate rapidly, and then the strong luminescent properties of BODIPY were restored Using this fast reversible reaction process, a high-efficiency probe for formaldehyde was designed The probe system can detect 0.1ppb formaldehyde in 10s, and the fluorescence response to 5-equivalent formaldehyde can reach 120000 times It provides a new system and theoretical basis for the design and application of a new fluorescent probe Relevant work was recently published in nature commun 2018, 9:362 (DOI: 10.1038 / s41467-017-02270-0) Thesis link: https:// Yang Guoqiang researcher research group: http://gqyang.iccas.ac.cn/labhead Yang Guoqiang researcher