合成化学2024,Vol.32Issue(7) :649-656.DOI:10.15952/j.cnki.cjsc.1005-1511.24005

多芳基氮杂氟硼二吡咯的合成及其光热性质

Synthesis and Photothermal Properties of Polyaryl Aza-BODIPY

李晓涵 孟祥龙 盛万乐
合成化学2024,Vol.32Issue(7) :649-656.DOI:10.15952/j.cnki.cjsc.1005-1511.24005

多芳基氮杂氟硼二吡咯的合成及其光热性质

Synthesis and Photothermal Properties of Polyaryl Aza-BODIPY

李晓涵 1孟祥龙 1盛万乐2
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作者信息

  • 1. 蚌埠医科大学癌症医学转化重点实验室,安徽蚌埠 233030
  • 2. 蚌埠医科大学癌症医学转化重点实验室,安徽蚌埠 233030;安徽师范大学安徽分子基材料重点实验室,安徽芜湖 241001
  • 折叠

摘要

具有较高光热效率的近红外有机染料在光热治疗领域有很好的应用前景.本文以氮杂氟硼络合物(Aza-BODIPY)作为研究对象,利用溴化反应和Suzuki偶联,合成了 3种具有多芳基氮杂氟硼二吡咯化合物.探究了这3种具有多芳基Aza-BODIPY化合物的最大吸收峰以及光热性能与芳基数量的关系.结果表明:四到六芳基Aza-BODIPY在CH2CI2的最大吸收峰分别为691 nm、684 nm和680 nm,这说明随着Aza-BODIPY的芳基数量增加,化合物的吸收光谱并没有明显红移.光热实验表明:多芳基Aza-BODIPY其具有较高的光热转化效率.以二甲苯作为溶剂,配制成20 μg/mL的溶液,四到六芳基Aza-BODIPY光热转换效率分别为75.4%、77.3%和76.8%.说明在Aza-BODIPY的2-位和6-位引入芳基对光热效应的促进作用很有限.这可能是因为芳基数量增加会造成基团之间变得拥挤,使得基团的旋转受阻,综合表现光热效应增加不显著.本论文证明了在Aza-BODIPY的2,6-位引入芳基不能使光谱红移,可以略微地提高光热转换效率.

Abstract

Near-infrared organic dyes with high photothermal efficiency have a promising application in the field of photothermal therapy.In this article,we take Aza-BODIPY as the research object,and synthesize three polyarylaza BODIPY compounds by using bromination and Suzuki coupling reaction.Explore the relationship between the maximum absorption peaks and photothermal properties with the number of aromatic groups of these three Aza-BODIPY compounds.In CH2Cl2,the maximum absorp-tion peaks of four to six aryl Aza-BODIPY are tested to be 691 nm,684 nm and 680 nm.This results indicating that with the increase of the aryl group of Aza-BODIPY,the absorption spectrum of the com-pounds does not show a significant red-shifted.Photothermal experiments have shown these Aza-BODIPY compounds have high photothermal conversion efficiency.When prepared into a solution of 20μg/mL using dimethyl sulfoxide as a solvent,the photothermal conversion efficiency is 75.4%,77.3%,and 76.8%,respectively.The effect of aryl in 2,6-position of Aza-BODIPY on photothermal is limited.It may be because increase the number of aryl groups will cause the crowding between the groups,so that the rotation of the groups was blocked,and the increase of photothermal conversion efficiency was not significant.This paper proved that the introduction of aryl group at the 2,6-position of Aza-BODIPY can't redshift the spectrum,but can slightly improve the photothermal conversion efficiency.

关键词

氮杂氟硼二吡咯/Suzuki反应/近红外/吸收/光热

Key words

aza-BODIPY/Suzuki reaction/near-infrared/absorption/photothermal

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基金项目

蚌埠医学院自然科学基金资助项目(2022byfy006)

安徽分子基材料重点实验室开放项目(fzj2208)

出版年

2024
合成化学
四川省化学化工学会 中国科学院成都有机化学研究所

合成化学

CSTPCD
影响因子:0.42
ISSN:1005-1511
参考文献量1
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