Branchy porphyrin molecule with the characteristics of intramolecular energy transfer and two-photon absorption

A technology of two-photon absorption and energy transfer, applied in the field of porphyrin derivatives, can solve the problems of unfavorable photosensitizer absorption, weak linear absorption, affecting practical application, etc., and achieve the effect of excellent optical performance and strong two-photon absorption.

Active Publication Date: 2007-06-06
苏州恒久光电科技股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the weak linear absorption of porphyrin derivatives in the wavelength > 600nm region, it is not conducive to the absorption of light by photosensitizers in tissues, which affects its practical application in photodynamic cancer therapy (PDT).

Method used

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  • Branchy porphyrin molecule with the characteristics of intramolecular energy transfer and two-photon absorption
  • Branchy porphyrin molecule with the characteristics of intramolecular energy transfer and two-photon absorption
  • Branchy porphyrin molecule with the characteristics of intramolecular energy transfer and two-photon absorption

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Synthesis of 5,10,15,20-tetrakis-[4-E-(diphenylamino)styryl)]-tetraphenylporphyrin (abbreviated as TPPX4).

[0043] (1) Add 1.86g (0.01mol) p-bromobenzaldehyde and 45mL propionic acid into a 250mL three-necked flask, reflux at 140°C, dissolve 0.7g freshly distilled pyrrole in 15mL propionic acid, slowly drop into the flask, and react 80min, cooled to room temperature, left standing, suction filtered, washed with propionic acid, dried to obtain 0.55g purple powder: 5,10,15,20-tetra-(4-bromo)-tetraphenylporphyrin (abbreviated as TPP- Br4). Yield 23.70%. Mp>300℃. 1 H NMR (CDCl 3 ;400MHz; Me 4 Si): δ, ppm-2.87(s, 2H, NH), 7.89-7.91(d, 8H, J=8.4Hz), 8.06-8.08(d, 8H, J=8.4Hz).

[0044] (2) In a closed device, 0.28g (0.31mmol) TPP-Br4, 0.5g (1.85mmol) 4-E-(diphenylamino) styrene, 0.093g (0.31mmol) o-methyltriphenyl Add phosphine into the reaction flask, inject nitrobenzene (15mL) and tributylamine (15mL) and a small amount of catalyst, and react under reflux a...

Embodiment 2

[0045]Example 2: 5,10,15,20-four-{two-[4-E-(diphenylamino)styrene]-N-4-E-(diphenylamino)styrene}tetraphenylporphyrin (TPPX12 for short) synthesis.

[0046] The method is similar to Example 1, only need to change 4-E-(diphenylamino)styrene in step 2 into 4,4'-bis-(4-E-(diphenylamino)styrene according to the obtained compound Base-N-4-E-(diphenylamino)styrene. Use chloroform / petroleum ether (1:1 v / v) as the mobile phase to pass through the silica gel column, take the second phase red component, and obtain the product purple Solid, 4.1% yield.

Embodiment 3

[0047] Example 3: Synthesis of 5,10,15,20-tetra-[4-E-(N-carbazolyl)styryl]-tetraphenylporphyrin (TPPCz4 for short).

[0048] Similar to Example 1, it is only necessary to change 4-E-(diphenylamino)styrene in step 2 to 4-E-N-carbazole styrene according to the obtained compound. Yield 8.3%. Mass spectrum (MALDI-TOF-TOF): 1685 (M + ), 1417 (fragmentation peak, loss of 1 4-N-carbazole styryl group), 1150 (fragmentation peak, loss of 2 4-N-carbazole styryl groups). 1 H NMR (CDCl 3 ;400MHz; Me 4 Si): δ (ppm), -2.540 (s, 2H, -NH porphyrin), 7.327-7.376 (q, 4H, J = 6.5Hz, double bond), 7.463-7.513 (q, 4H, J = 6.6Hz, double bond), 7.534, 7.560, (d, 8H, J=10.4Hz, phenyl), 7.794, 7.874 (d, 8H, J=8.0Hz, phenyl), 7.956-8.037 (m, 16H, J=8.1Hz, phenyl ), 8.291-8.387 (m, 16H, phenyl), 8.678-8.587 (m, 16H, phenyl), 8.867 (s, 8H, pyrrole, β-H protons).

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Abstract

The present invention discloses one kind of branchy porphyrin molecule with the characteristics of intramolecular energy transfer and two-photon absorption, and features that the branchy porphyrin molecule is symmetric or asymmetric conjugated branchy molecule with porphin ring as core and triphenylamine element or carbazolyl radical as branch. The compound of the present invention has excellent optical performances, including strong two-photon absorption in both 532 nm and 800 nm bands and powerful up converting transmission in 650-750 nm band. It may be used in photodynamic treatment of two-photon absorption mechanism, light limitation in two-photon absorption mechanism and photovoltaic solar cell material.

Description

technical field [0001] The present invention relates to a class of porphyrin derivatives, in particular to a class of symmetrical and asymmetrical conjugated multi-branched compounds with a porphine ring as the "core" and containing a diphenylamino group or a carbazole group, which have strong two-photon absorption properties and remarkable intramolecular energy transfer properties. Background technique [0002] Two-photon absorption (TPA) is a process in which a medium molecule absorbs two photons simultaneously to transition from the ground state to the excited state under strong light excitation. It is characterized in that medium molecules have small absorption and dispersion of longer light waves, strong penetration ability of light waves, and the transition probability is proportional to the square of incident light intensity; under the condition of tight focusing of laser beams, the excited range of medium molecules is limited to lambda 3 W...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22H01L51/46
CPCY02E10/50Y02E10/549
Inventor 王筱梅杨平王保柱李文磊张唯舟
Owner 苏州恒久光电科技股份有限公司
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