高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (8): 1676-1682.doi: 10.7503/cjcu20180157

• 有机化学 • 上一篇    下一篇

基于三苯胺的双氰基二苯代乙烯型双光子荧光溶剂生色探针

黄池宝(), 潘淇, 陈华仕, 梁兴, 吕国岭   

  1. 遵义师范学院化学化工学院, 遵义 563002
  • 收稿日期:2018-02-28 出版日期:2018-08-10 发布日期:2018-06-20
  • 作者简介:联系人简介: 黄池宝, 男, 博士, 教授, 主要从事双光子荧光探针方面的研究. E-mail: huangchibao@163.com
  • 基金资助:
    贵州省高层次创新型人才培养计划项目——“百”层次人才(批准号: 黔科合平台人才[2016]5683)、 国家自然科学基金(批准号: 21562050)、 贵州省第八批科技创新人才团队建设专项基金[批准号: 黔科合人才团队(2015)4007]、 贵州省科学技术基金项目(批准号: 黔科合J字[2015]2146)、 贵州省教育厅自然科学重点研究项目(批准号: 黔教合KY字[2014]296)、 贵州省教育厅省级本科教学工程建设项目(批准号: 黔教[2014]JXGChcb)、 遵义市“15851人才精英工程”项目[批准号: (2015)4007]和遵义市红花岗区科学技术项目(批准号: 遵红科合社字[2015]18)资助.

Triphenylamine-based Dicyanostilbene Type Two-photon Fluorescence Solvatochromic Probe

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

  1. College of Chemistry and Chemical Engineering, Zunyi Normal University, Zunyi 563002, China
  • Received:2018-02-28 Online:2018-08-10 Published:2018-06-20
  • Contact: HUANG Chibao E-mail:huangchibao@163.com
  • Supported by:
    † Supported by the High-level Innovative Talents Training Project——Hundred Talents Program of Guizhou Province, China(No. [2016]5683), the National Natural Science Foundation of China(No. 21562050), the Special Fund 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 Honghuagang District of Zunyi City, China(No. [2015]18).

摘要:

以双氰基二苯代乙烯为双光子荧光母体, 借助电子供体-π-电子受体(D-π-A)构-效关系, 以二苯氨基作电子供体, 氰基作电子受体, 开发了一个新型的双光子荧光溶剂生色探针(SP1), 并对其结构进行了表征. 性能测试结果表明, SP1在环己烷和二甲亚砜(DMSO)中的最大发射波长分别为452和604 nm, 显示出很宽的溶剂生色范围(152 nm), 可用于溶剂极性与黏度的检测, 亦能根据最大发射波长识别溶剂种类. SP1拥有较大的双光子吸收截面, 在环己烷和DMSO中的最大双光子吸收截面分别为6670和2040 GM, 并具有较大的斯托克斯位移(194 nm), 其光稳定性、 水溶性和细胞渗透性均比较优良. 该探针可用于细胞中黏度的检测与成像.

关键词: 双光子荧光溶剂生色探针, 溶剂极性, 黏度, 细胞成像

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

中图分类号: