Triphenylamine-based Dicyanostilbene Type Two-photon Fluorescence Solvatochromic Probe†

doi:10.7503/cjcu20180157

Abstract

Abstract:

Using the diphenylamino group as the electron donor, the cyano group as the electron acceptor, and the dicyanostilbene as a two-photon fluorophore, a novel two-photon fluorescence solvatochromic probe(SP1) was developed by means of the structure-activity relationship of D-π-A(D: electron donor, A: electron acceptor) electron architecture. The structure was characterized and identified by means of nuclear magnetic resonance spectra and element analysis instrument. SP1 showed a wide range of 152 nm in solvent solvatochromism, the maximum emission wavelengths in cyclohexane and dimethylsulfoxide(DMSO) were 452 and 604 nm, respectively. It can be used for the detection of solvent polarity and viscosity. Solvents can also be identified according to maximum emission wavelengths. SP1 had a large two-photon absorption cross section, the maximum two-photon absorption cross-sections in cyclohexane and DMSO were 6670 and 2040 GM, respectively, and also had a large Stokes shift(194 nm). Its photostability, water solubility and cell permeability were excellent. The probe can be used for the measurement and imaging of cell viscosity.

Key words: Two-photon fluorescence solvatochromic sensor, Solvent polarity, Viscosity, Cell-imaging

CLC Number:

O625

TrendMD:

HUANG Chibao, PAN Qi, CHEN Huashi, LIANG Xing, LÜ Guoling. Triphenylamine-based Dicyanostilbene Type Two-photon Fluorescence Solvatochromic Probe^†[J]. Chem. J. Chinese Universities, 2018, 39(8): 1676.

Figures/Tables 9

Scheme 1 Molecular structure and synthetic procedure of SP1

Fig.1 Normalized absorption(A) and one-photon emission spectra(B) of SP1 in various solventsc(SP1)(absorption)=10 μmol/L, c(SP1)(emission)=1 μmol/L, λex(OP)=412 nm.

Fig.2 Pictures of fluorescence of SP1 in different solvents(c=1 μmol/L, λex=365 nm)

Scheme 2 Charge separation profile of SP1

Fig.3 Normalized one-(A) and two-photon(B) emission spectra of SP1 in glycerol-ethanolOne-photon λex=412 nm; two-photon λex=810 nm; c(P2)=1 μmol/L; g: glycerol, e: ethanol.

Fig.4 One-photon emission spectra(A) and linear fitting curve(B) in a double-logarithmic scale of SP1 in various viscosity(glycerol-ethanol solution)c(SP1)=1 μmol/L, λex(OP)=412 nm, 20 ℃.

Fig.5 Two-photon absorption cross sections of SP1(0.1 μmol/L) in various solvents vs. two-photon excited wavelengths

Fig.6 Bright-field two-photon excitation fluorescence image(A) and two-photon microscopy image of 1 μmol/L SP1-labeled(B) and 4 μmol/L X1-labeled(C) mouse fibroblast collected at 550—650 nmThe two-photon excitation fluorescence(TPEF) images were collected upon excitation at 800 nm with a femtosecond pulse.Cells shown were representative images from replicate experiments(n=5).

Fig.7 Response curve of fibroblast to SP1 dose from 0 to 50 μmol/L for 24 hData presented as percentage of control(n=3)±SD,SD: standard deviation, P<0.01.

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