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Diphenylacetylene-containing cyclopentadienyl iron salt two-photon absorption materials and preparation method thereof

A two-photon absorption, cyclopentadienyl iron technology, applied in the directions of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of poor resin compatibility and complex synthesis process, and achieve a simple and good preparation process. The effect of compatibility

Active Publication Date: 2015-06-17
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compounds that have been developed above generally have problems such as complex synthesis process and poor compatibility with resins.

Method used

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  • Diphenylacetylene-containing cyclopentadienyl iron salt two-photon absorption materials and preparation method thereof
  • Diphenylacetylene-containing cyclopentadienyl iron salt two-photon absorption materials and preparation method thereof
  • Diphenylacetylene-containing cyclopentadienyl iron salt two-photon absorption materials and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]In the invention, the initial substance is p-bromoaniline, the intermediate product p-bromoiodobenzene is prepared by diazotization reaction, and then it is connected with phenylacetylene by Sonogashira coupling reaction to obtain another intermediate product bromotoluene; with 4- Bromophenol is prepared as a raw material to obtain 4-hydroxyphenylboronic acid, which is then reacted with brominated tolanylacetylene by Suzuki coupling to obtain 4-(phenylethynyl) biphenol, which is then combined with [( n 6 - 1,4 - Dichlorobenzene)-iron-( n 5 - Cyclopentadiene)] hexafluorophosphate reaction to obtain [( n 6 -1,4-bis(phenylethynylbiphenoxy)benzene)-iron-( n 5 -cyclopentadiene)] hexafluorophosphate. Concrete synthetic route is shown as follows:

[0045]

[0046] In the formula:

[0047] a: NaNO 2 , HCl, 0-5°C, react for 0.5 hours, KI;

[0048] B: ditriphenylphosphine palladium dichloride, triphenylphosphine, cuprous iodide;

[0049] c: TBDMSCl, Mg, THF, B(...

Embodiment 2

[0070] In the invention, 4-(2-phenylethynyl)-bromobenzene (synthetic method is the same as in Example 1) is utilized to prepare 4-(2-phenylethynyl) phenylboronic acid, and then reacted with [(η 6 -1,4-dichlorobenzene)-iron-(η 5 -Cyclopentadiene)] hexafluorophosphate is connected to obtain the target compound [( n 6 -1,4-diphenylethynylbiphenyl)-iron-( n 5 -cyclopentadiene)] hexafluorophosphate. Concrete synthetic route is shown as follows:

[0071]

[0072] (1) Preparation of 4-phenylacetylene boronic acid

[0073]

[0074] In a 100ml three-neck flask, add 2g (7.78mmol) of 4-(2-phenylethynyl)-bromobenzene and 30ml of tetrahydrofuran, start stirring, protect with nitrogen to dissolve, and cool down to -78°C with an acetone-liquid nitrogen bath. Add 5.3ml (8.5mmol) of 1.6M n-butyllithium cyclohexane solution dropwise to the system, keep at -78°C, react for 0.5 hours, and add 1.21g (11.67mmol) trimethyl borate dropwise to the system. After the dropwise addition, th...

Embodiment 3

[0080] Same as the preparation method of Example 1, just change the reactant into p-iodophenol and 4-methoxyphenylacetylene to react to prepare 4-(4-methoxy)phenylacetylene phenol, and [( n 6 - 1,4 - Dichlorobenzene) -Iron-( n 5 - cyclopentadiene)] hexafluorophosphate to obtain the target product [( n 6 -1,4-bis((4-methoxyphenylethynyl)phenoxy)benzene)-iron-( n 5 -cyclopentadiene)] hexafluorophosphate. Concrete synthetic route is shown as follows:

[0081]

[0082] (1) Preparation of 4-methoxyphenylacetylene

[0083] Add NaOH 4.16g (0.104mol) and water 17ml into a 250ml three-necked flask, heat to reflux, and dropwise add ( Z )-3-Chloro-3-(4-methoxyphenyl)acrolein 19.6g (0.1mol) in 1,4-dioxane solution, the dropwise addition was completed, and the reaction was carried out for 4 hours, and the reaction progress was tracked by TLC. After the reaction was completed, cool to room temperature, stand to separate the layers, separate the organic phase, extract th...

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Abstract

The invention relates to three cyclopentadienyl iron salt two-photon absorption materials having a diphenylacetylene group and a preparation method thereof; a diphenylacetylene structure and a cationic cyclopentadienyl iron receptor are jointly composed of a D-(pi)-A type two-photon absorption functional group, and thus the three synthesized novel cyclopentadienyl iron salts have a strong two-photon absorption ability at 532 nm, and has great application value in the two-photon photoetching field when used as the two-photon absorption type cationic photo-initiator.

Description

technical field [0001] The invention belongs to the technical field of photosensitive materials, and in particular relates to cyclopentadienyl iron salt compounds with tolanyl groups having two-photon absorption and a preparation method thereof. Background technique [0002] The two-photon process is long-wave absorption and short-wave emission. The absorption process has a high degree of three-dimensional space selectivity and high penetration. It is used in three-dimensional information storage, photodynamic therapy, optical limiting, stereolithography, and two-photon fluorescence microscopy. It has broad application prospects. However, the probability of two-photon absorption in ordinary molecules is very small, and only at the focal point where the beam is focused can two photons be absorbed at the same time, so high-power excitation light is usually required. The development of materials with strong two-photon absorption has become a research hotspot. Two-photon mater...

Claims

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Application Information

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IPC IPC(8): C07F17/02C09K11/06
CPCC07F17/02C09K11/06C09K2211/187
Inventor 王涛李光雷王孟强
Owner BEIJING UNIV OF CHEM TECH
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