Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (11): 1485-1493.DOI: 10.6023/A22060267 Previous Articles     Next Articles



王其a, 夏辉a, 熊炎威a, 张新敏a, 蔡杰a, 陈冲b, 高逸聪a, 陆峰a,*(), 范曲立a,*()   

  1. a 南京邮电大学 有机电子与信息显示国家重点实验室 信息材料与纳米技术研究院 南京 210023
    b 南京理工大学 医院 南京 210094
  • 投稿日期:2022-06-21 发布日期:2022-10-09
  • 通讯作者: 陆峰, 范曲立
  • 基金资助:
    国家自然科学基金(22175098); 国家自然科学基金(21975131); 江苏省博士后科研资助计划(2021K114B); 江苏省高等学校自然科学研究面上项目(21KJB430031); 南京邮电大学校级科研基金(NY220198)

Simple Preparation of Near-infrared-II Organic Small Molecule-based Phototheranostics by Manipulation of the Electron-donating Unit

Qi Wanga, Hui Xiaa, Yanwei Xionga, Xinmin Zhanga, Jie Caia, Chong Chenb, Yicong Gaoa, Feng Lua(), Quli Fana()   

  1. a State Key Laboratory for Organic Electronics and Information Displays, Institute of Advanced Materials, Nanjing University of Posts & Telecommunications, Nanjing 210023, China
    b Hospital, Nanjing University of Science and Technology, Nanjing 210094, China
  • Received:2022-06-21 Published:2022-10-09
  • Contact: Feng Lu, Quli Fan
  • Supported by:
    National Natural Science Foundation of China(22175098); National Natural Science Foundation of China(21975131); Postdoctoral Science Foundation of Jiangsu Province(2021K114B); Natural Science Foundation of the Jiangsu Higher Education Institutions(21KJB430031); Scientific Fund of Nanjing University of Posts and Telecommunications(NY220198)

Organic small molecules hold great promise in the field of phototheranostics by virtue of their clear chemical structure, outstanding biocompatibility, and distinguished repeatability. Whereas the synthetic process of them suffers from multi-step and complex reactions. Meanwhile, most of small molecules employed near-infrared-I (NIR-I) fluorescence imaging, which could not effectively provide comprehensive tumor information with high resolution. In addition, the reported small molecules showed unsatisfactory singlet oxygen yield and photothermal conversion efficiency, limiting their extensive application in cancer theranostics. Herein, by conjugating diketopyrrolopyrrole (an electron-withdrawing unit) with benzene, aniline, or 1,2-diaminobenzene (electron-donating units), respectively, three novel small molecules DPP-0, DPP-2 and DPP-4 were designed and synthesized by one-step reaction. DPP-0 NPs, DPP-2 NPs and DPP-4 NPs as phototheranostics were further obtained through nanoprecipitation method by self-assembling with Pluronic F127. It was found that with the increase of amino groups, the absorption/emission peaks of NPs were red-shifted. Especially, DPP-4 NPs exhibited strong absorption in the NIR-I region, and the maximum emission peak of DPP-4 NPs was located in the near-infrared-II (NIR-II) region, suggesting that the optical properties of small molecules can be regulated by changing the electron-donating unit. After irradiation of DPP-4 NPs with a single laser, excellent NIR-II fluorescence signal can be obtained for efficient imaging of tumor with high resolution. Moreover, abundant reactive oxygen species (singlet oxygen yield 34.3%) and hyperthermia (photothermal conversion efficiency 40.2%) can also be produced by irradiation of DPP-4 NPs, realizing the combined photodynamic/photothermal therapy guided by NIR-II fluorescence imaging.

Key words: organic small molecule, phototheranostics, near-infrared-II fluorescence imaging, photodynamic therapy, photothermal therapy