Highly Sensitive Dicyanostilbene Two-photon Fluorescence Probe for Temperature
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School of Information Engineering, Zunyi Normal University

Clc Number:

O625.34;O625.63;O625.72

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This work was supported by the Guizhou Province High-level Innovative Talents Training Project──Hundred Talents Program (No. (2016)5683), Science and Technology Project in Guizhou Province (No. [2020]4Y001), the Special Fund Project of the Construction of the Eighth Batch of Scientific and Technological Innovation Talent Team in Guizhou Province [No. (2015)4007], Guizhou Science and Technology Fund Project (No. J[2015]2146), the Key Project of Education Department of Guizhou Province (No. KY[2014]296)

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    Abstract:

    A novel two-photon fluorescence environment sensitive probe 2,5-dicyano-4-methyl-4’-(9-carbazolyl) stilbene (SP) with the push-pull electronic architecture (Donor-π-Acceptor (D-π-A)) derived from dicyanostilbene was developed. The unusually sensitive solvatochromism of SP varied from 412 nm in cyclohexane to 541 nm in DMSO in the emission maximum wavelengths. Compound SP with remarkably large two-photon absorption cross section (δTPA, δTPA = 6930 GM) exhibited very strong polarity- and temperature-dependence of fluorescence. The fluorescence quantum yield (Φ) of SP was quite high, and its maximum value reached 0.992 in cyclohexane. Its linearly dependent coefficients (R2) between the one- and two-photon emission intensities of SP and temperatures all reached 0.998 in both one-photon emission (OPE) and two-photon emission (TPF), and the function expressions were IF = -0.0141T + 1.2881 (OPE) and IF = -0.0143T + 1.2698 (TPE) (IF: fluorescence intensity; T: temperature (℃)), respectively. This clearly indicated that SP is a considerably ideal temperature probe and can also be used to detect polarities of solvents. SP is therefore also called an environment-sensitive probe. The successful applications of SP provide a brilliant prototype (relatively small molecule, high δTPA and Φ) for the developments of ideal two-photon fluorescence temperature probes.

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History
  • Received:May 22,2023
  • Revised:July 27,2023
  • Adopted:July 17,2023
  • Online: April 10,2024
  • Published:
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