芳并氮杂氟硼二吡咯的合成与应用

Synthesis and application of aromatic rings fused AzaBODIPY

芳并氮杂氟硼二吡咯染料因具有近红外吸收发射且易于修饰和衍生而被广泛应用于生物医学和材料科学等前沿领域.本文在介绍芳并氮杂氟硼二吡咯染料构建策略的基础上,着重介绍了本课题组近年来在芳并氮杂氟硼二吡咯染料的构建、修饰衍生、性能及应用等方面所取得的最新研究进展.其中,[a]芳并氮杂氟硼二吡咯的构建主要通过邻芳基二腈路线和芳并吡咯的亚硝化、缩合及后续氟硼配位的从头合成路线来实现;[b]芳并以及全并氮杂氟硼二吡咯的构建通过金属催化的碳氢活化和分子内氧化脱氢偶联实现.后续研究发现这些新型近红外染料呈现出良好的生物成像、光热治疗及半导体性能.最后,本文围绕这类染料的合成及应用前景进行了展望.

Aromatic rings fused BF2azadipyrromethenes(AzaBODIPY)exhibit wide applications in frontier fields such as biomedicine and materials science due to their unique near-infrared absorption,emission,simple synthesis,modification and derivatization.Based on the modified strategies of aromatic rings fused AzaBODIPY dyes,this review mainly focuses on the latest research progress of the construction strategy,the regulatory of optoelectronic properties and the application of near-infrared AzaBODIPY dyes made by our group in recent years.Among those,[a]-aromatic rings fused AzaBODIPYs are mainly conducted by phthalodinitrile route and the route of totally synthetic aromatic pyrroles by nitrosation,condensation,and BF2chelation.And[b]-aromatic rings and[a,b]-aromatic rings annularly fused AzaBODIPYs are conducted by metal-catalyzed C–H activation or intramolecular dehydrogenation oxidation coupling reactions.Further researches indicate that these novel near infrared dyes exhibit advantageous bioimaging,therapy and semiconducting characteristics.Finally,the synthesis,application and development of these dyes have been discussed.