摘要
远红/近红外(FR/NIR)发射荧光材料因其在生物成像领域的巨大应用潜力而受到广泛关注.然而,根据“能隙”规则,电子带隙减小时,非辐射失活途径占据能量耗散主导地位,因此制备高量子产率、长发射波长的有机FR/NIR材料仍然是一个挑战.本文通过引入扭曲构象基团(四苯基乙烯)对分子聚集态进行调控,合成了一系列基于苯并硒二唑的供体-受体-供体(D-A-D)型化合物.化合物TPE-DPA-Se在纳米粒子状态下表现出明亮的荧光发射,其量子产率可高达16.48%,证明其在水体系中仍具有良好的发射性能,适用于多个领域.本研究进一步证实了其优秀的细胞成像能力,并将其成功地应用于荧光成像引导的手术导航,特别是微小转移瘤的术中检测.
Far red/near infrared(FR/NIR)materials have attracted wide attention due to their great potential in various ap-plications,particularly in bio-imaging.However,it is still a challenge to manufacture organic FR/NIR materials with quite high efficiency and long emission wavelength,owing to the dominance of non-radiative deactivation in the dissipation of absorbed light excitation energy when the electronic bandgap decreases.Herein,a series of donor-acceptor-donor(D-A-D)type compounds based on benzoselenidazole are developed through the regulation of molecular aggregation states by twisted conformation groups.In one hand,the compound TPE-DPA-Se(tetraphenylethylene-diphenylamine-benzoselenidazole)ex-hibits the best aggregation-induced emission(AIE)properties among these compounds.In another hand,the obtained TPE-DPA-Se showed over 150 nm Stokes shift,which can be used to avoid the interference between excitation and emission light,as well as the near-infrared emission spectrum away from the organism auto-fluorescence,which was beneficial for the bio-application.Next,density functional theory(DFT)calculation was carried out with Gaussian 09W program at B3LYP/6-31G**level to determine the highest occupied molecular orbital(HOMO),the lowest unoccupied molecular orbital(LUMO)distributions and the optimized structures of these compounds.Then TPE-DPA-Se was formulated into nanoparti-cles by nanoprecipitation method with an amphiphilic co-polymer 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000](MPEG2000-DSPE)as the doping matrix.TPE-DPA-Se exhibited excellent aqueous diameter stability in nanoparticle-state,as well as impressive luminescence in aqueous system with higher efficiency of up to 16.48%,which are suitable for many fields.To evaluate the biocompatibility of the TPE-DPA-Se NPs,we further carried out 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide(MTT)cytotoxicity assay.The result indicated their negligible toxicity.Encouraged by the excellent performance of these lum
作者
高贺麒
焦迪
欧翰林
章经天
丁丹
Heqi Gao;Di Jiao;Hanlin Ou;Jingtian Zhang;Dan Ding(State Key Laboratory of Medicinal Chemical Biology,Key Laboratory of Bioactive Materials,Ministry of Education,College of Life Sciences,Nankai University,Tianjin 300071,China)
出处
《化学学报》
SCIE
CAS
CSCD
北大核心
2021年第3期319-325,共7页
Acta Chimica Sinica
基金
国家自然科学基金(Nos.51961160730,51873092,81921004)
国家重点研发计划、中国-澳大利亚政府间国际科技创新合作项目(2017YFE0132200)
天津市杰出青年科学基金(19JCJQJC61200)资助.
关键词
聚集诱导发光
远红/近红外
纳米粒子
细胞成像
手术导航
aggregation-induced emission
far red/near-infrared
nanoparticles
cell imaging
surgical navigation
