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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: 2005-01-26
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] 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

[0030] Example 1: 2,7-bis[(2-4'-ethoxyphenyl-5-4'-styryl)-1,3,4-oxadiazole]thiafluorene and its synthesis.

[0031] (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-necked round-bottomed flask in turn, and reflux for 1- 4 days. The solvent was distilled off, and 20 g of white solid 4-ethoxybenzohydrazide (a) was obtained by suction filtration, mp: 125-128°C.

[0032] (2) Compound (a), pyridine, and tetrahydrofuran were mixed in a beaker. The mixed solution was slowly added into 15.4 g of 4-methylbenzoyl chloride under stirring, and a white precipitate was formed immediately. After stirring at room temperature for several hours, it was slowly poured into ice water, allowed to stand overnight, filtered, and recrystallized from absolute ethanol to obtain 8.3 g of bishydrazide intermediate (b).

[0033] (3) Add POCl in turn to the round bottom flask 3 and intermediate (b), N 2...

Embodiment 2 to Embodiment 21

[0041] Example 2 to Example 21: The synthesis method is similar to Example 1, only need to change the 4-ethoxy ethyl benzoate in step (1) and the 2,7- Thiofluorenedial.

[0042] The general formula of the compound is,

[0043]

[0044] 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(CH 3 ) 3

NC 2...

Embodiment 22

[0048] Embodiment 22: Prepared according to the following steps,

[0049] (1) Dissolve 1-cyano-3,5-benzenedicarboxylic acid in 50ml SOCl 2 10ml of pyridine was added dropwise, and refluxed at 55°C for 7 hours to obtain a dark brown transparent liquid. Excess SOCl 2 and pyridine were distilled off under reduced pressure to obtain 1,3-diacyl chloride benzocyanide as a yellow solid.

[0050] (2) 9.36g (0.052mol) of 4-ethoxybenzohydrazide was dissolved in a mixture of THF and pyridine, then added dropwise to 1,3-diacylchloride benzocyanide, stirred at room temperature for 4 to 6 hours, The THF was distilled off under reduced pressure, the remaining liquid was poured into water, and a white solid precipitated after standing for 2 hours, filtered by suction and washed with ethanol to obtain 8 g of intermediate product (I), with a yield of 66%. M.p.252-255°C. 10g (0.021mol) of intermediate product (I) was dissolved in 125ml POCl 3 In, the reaction solution in N 2 It was refluxe...

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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 heterofluorene ring as a symmetrical center and a symmetrical conjugated structure containing oxadiazole, which has strong two-photon absorption performance. Background technique [0002] Since the advent of laser, nonlinear optics has developed rapidly, and the development of high-efficiency 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 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 process is characterized by the fact that the medium has small absorption and dispersion of light with a longer wavelength, and the light wave has a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14
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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