Two-photon fluorescent dye based on phenyl-substituted boron-dipyrromethene and diphenyl indenofluorene and synthetic method thereof

Abstract

The invention discloses two-photon fluorescent dye based on phenyl-substituted boron-dipyrromethene and diphenyl indenofluorene; the two-photon fluorescent dye has a structural general formula shown in the description, wherein R is C1-C18 alkyl; the synthetic steps include: using 2,4-dimethylpyrrole and benzaldehyde as raw materials to generate 5-phenyl-substituted and 2,6-iodide boron-dipyrromethene; reducing indenofluorene dione, alkylating, brominating, carrying out Pd(0) catalytic amination, carrying out Pd(0) and CuI catalyzed Sonogashira cross-coupling reaction, and removing trimethylsilyl to generate diphenylamine-indenofluorene-ethynyl compound; enabling the 2,6-iodide boron-dipyrromethene to react with the diphenylamine-indenofluorene-ethynyl compound to obtain the two-photon fluorescent dye; the two-photon fluorescent dye has high two-photon fluorescence, maximum two-photon absorption section in toluene reaches 776 GM, fluorescent quantum yield reaches 0.46, and a new idea to synthesize and apply two-photon fluorescent dyes based on boron-dipyrromethene is provided.

Description

technical field [0001] The invention belongs to the technical field of fluorescent dyes, and in particular relates to a two-photon fluorescent dye based on phenyl-substituted fluoroboron dipyrrole and dianilinoindenofluorene and a synthesis method thereof. Background technique [0002] Two-photon absorption is a third-order nonlinear optical effect. Organic materials with large two-photon absorption cross-sections have applications in three-dimensional optical storage, two-photon fluorescence imaging, two-photon optical limiting materials, and photodynamic therapy [4] and other fields have broad application prospects. In the research field of two-photon fluorescent dyes, the development of fluorescent dyes with larger two-photon absorption cross section is the key. [0003] Fluoroboron dipyrrole is a class of fluorescent chromophores with excellent performance. It has a large molar extinction coefficient, high fluorescence quantum yield, good photostability, good tolerance...

AI Technical Summary

Problems solved by technology

For example, Wang et al. introduced alkynyl electron-donating groups at the 2 and 6 positions of fluoroboron dipyrrole, but the improvement of its two-photon absorption cross section was not obvious (29-60 GM)

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