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Heterofluorene derivative with strong two photon absorption character

A technology of two-photon absorption and derivatives, applied in organic chemistry and other fields, can solve the problems of high price and difficult synthesis of thiophene

Inactive Publication Date: 2006-04-05
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, trithiophene is expensive and difficult to synthesize, so organic molecules with it as the π-center are not ideal two-photon absorbing materials

Method used

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  • Heterofluorene derivative with strong two photon absorption character
  • Heterofluorene derivative with strong two photon absorption character
  • Heterofluorene derivative with strong two photon absorption character

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: 2,7-bis[(2-4'-ethoxyphenyl-5-4'-styryl)-1,3,4-oxadiazole] thiafluorene and its synthesis.

[0022] (1) Add 40.0g (0.206mol) of homemade ethyl 4-ethoxybenzoate, 30ml of hydrazine hydrate (30.9g, 0.617mol), and 200ml of absolute ethanol into a single-neck round-bottomed flask, and reflux for 1~ 4 days. The solvent was distilled off and filtered with suction to obtain 20 g of white solid 4-ethoxy benzoyl hydrazide (a), mp: 125-128°C.

[0023] (2) Mix compound (a), pyridine, and tetrahydrofuran in a beaker. Under stirring, the mixed solution was slowly added to 15.4g of 4-methylbenzoyl chloride, and a white precipitate was immediately formed. After stirring for several hours at room temperature, it was slowly poured into ice water, allowed to stand overnight, filtered, and recrystallized with absolute ethanol to obtain 8.3 g of bishydrazide intermediate (b).

[0024] (3) Add POCl sequentially to the round bottom flask 3 And intermediate (b), N 2 Reflux for 4-8 hours ...

Embodiment 2 to Embodiment 21

[0032]Example 2 to Example 21: The synthesis method is similar to that of Example 1. It only needs to change the ethyl 4-ethoxybenzoate in step (1) and the 2,7- in step (6) according to the obtained compound. Thiofluorene dialdehyde.

[0033] The general formula of the compound is,

[0034]

[0035] Example

R

X

Example 2

C(CH 3 ) 3

S

Example 3

F

S

Example 4

OC 2 H 5

O

Example 5

C(CH 3 ) 3

O

Example 6

F

O

Example 7

OC 2 H 5

NC 2 H 5

Example 8

OC 2 H 5

NC 4 H 9

Example 9

OC 2 H 5

NC 8 H 17

Example 10

OC 2 H 5

NC 12 H 25

Example 11

OC 2 H 5

NC 22 H 45

Example 12

C(CH 3 ) 3

NC 2 H 5

Example 13

C(CH 3 ) 3

NC 4 H 9

Example 14

C(CH 3 ) 3

NC 8 H 17

Example 15

C(CH 3 ) 3

NC 12 H 25

Example 16

C(...

Embodiment 22

[0039] Example 22: Prepared according to the following steps,

[0040] (1) Dissolve 1-cyano-3,5-phthalic acid in 50ml SOCl 2 In the medium, 10ml of pyridine was added dropwise and refluxed at 55°C for 7 hours to obtain a dark brown transparent liquid. Excess SOCl 2 Distilled with pyridine under reduced pressure to obtain 1,3-diacyl chloride benzocyanide as a yellow solid.

[0041] (2) Dissolve 9.36g (0.052mol) of 4-ethoxybenzoic acid hydrazide in the mixture of THF and pyridine, and then add dropwise to 1,3-diacyl chloride benzonitrile, and stir at room temperature for 4-6 hours. The THF was distilled off under reduced pressure, the remaining liquid was poured into water, and a white solid precipitated out after standing for 2 hours, filtered with suction and washed with ethanol to obtain 8 g of intermediate product (I) with a yield of 66%. M.p.252-255°C. Dissolve 10g (0.021mol) of intermediate product (I) in 125ml POCl 3 Yes, the reaction solution is in N 2 Reflux under the envir...

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PUM

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Abstract

The invention discloses a category of heterofluorene derivatives with strong two photon absorption character characterized in that, it is prepared from the symmetrical conjugation molecular by using the heterocyclic fluorine as the center of symmetry, wherein the hetero atoms in the heterocyclic fluorine are selected from S, O or N, and N atom has straight chain or branched chain alkyl, the elementary oxdiazole with electron suction capability is selected as the branch to construct conjugation multiple branch molecular material.

Description

Technical field [0001] The invention relates to a heterocyclic compound, in particular to a compound with a symmetrical conjugated structure that takes a heterofluorene ring as a symmetric center and contains oxadiazole, which has strong two-photon absorption performance. Background technique [0002] Since the advent of lasers, nonlinear optics has developed rapidly, and the development of efficient nonlinear optical materials has become one of the important topics in information technology. Two-photon absorption belongs to the third-order nonlinear optical effect, which means that under strong light excitation, the sample is excited by a light source that is nearly twice the linear absorption wavelength of the sample, so that it directly absorbs two photons through a virtual intermediate state and transitions to a high energy state. The characteristic of the process is that the medium has small absorption and dispersion of this long wavelength light, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/14C07D333/76C07D271/06
Inventor 王筱梅杨平杜玉扣刘国华郭晓稚陈建伟沈梁
Owner SUZHOU UNIV
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