Chem. J. Chinese Universities ›› 2019, Vol. 40 ›› Issue (6): 1128.doi: 10.7503/cjcu20190006

• Analytical Chemistry • Previous Articles     Next Articles

Dicyanostilbene-derived Two-photon Fluorescence Environment-sensitive Probe

HUANG Chibao(), PAN Qi, CHEN Huashi, LIANG Xing, LÜ Guoling   

  1. Chemistry and Chemical Engineering College, Zunyi Normal University, Zunyi 563002, China
  • Received:2019-01-04 Online:2019-06-10 Published:2019-05-11
  • Supported by:
    † Supported by the High-level Innovative Talents Training ProjectHundred Talents Program of Guizhou Province, China(No.[2016]5683), the National Natural Science Foundation of China(No.21562050), the Special Project of the Construction of the Eighth Batch of Scientific and Technological Innovation Talent Team in Guizhou Province, China[No.(2015)4007], the Science and Technology Fund Project of Guizhou Province, China(No.J[2015]2146), the Key Project of Education Department of Guizhou Province, China(No.KY[2014]296), the Teaching Contents and Curriculum System Reform Project of Higher Education in Guizhou Province, China(No.KY [2014] JXGChcb), the Project of “15851 Talents Elite Project” in Zunyi City, China(No.[2015]4007) and the Science and Technology Project of Zunyi City, China(No.[2015]18)

Abstract:

A novel two-photon fluorescence environment-sensitive probe(SP) with the push-pull electronic architecture derived from dicyanostilbene was developed. This was a typical example of the combination of solvatochromism and molecular rotor properties. The maximum emission wavelengths of the probe SP increased significantly with the increase of the polarities of the solvents, which was attributed to the transformation of the excited state molecule into one or more torsional intramolecular charge transfer states(TICT). Polar solvents were more conducive to the stability of the charge separation state molecule. In the TICT state, the fluorescence quantum yield of the molecule was strongly dependent on the polarity, viscosity and temperature of the solvent. The probe SP showed a fairly wide range of solvent solvatochromism, the maximum emissiom wavelengths were 445 in cyclohexane and 641 nm in dimethyl sulfoxide, respectively, and the gap was 196 nm. The probe SP was able to be used for the detection of solvent polarity, viscosity and temperature, and the recognition of solvent species. The probe SP also had large two-photon absorption cross sections, the maximum two-photon absorption cross sections were 5560 in cyclohexane and 130 GM in N,N-dimethylformamide, respectively, and a super-large Stokes shift which was 232 nm. The probe was able to be used for the measurement and imaging of cell viscosity.

Key words: Two-photon, Environment-sensitive sensor, Polarity, Viscosity, Cell-imaging

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