文献类型：期刊文献

英文题名：Thiaheptapyrrin and Thiatetrapyrrin Armed p-Phenylene-Bridged Norrole as NIR-II Dyes: Photothermal Behavior Effectively Enhanced by Protonation and Deprotonation

作者：Yang, Che[1,2];Lu, Hangchong[1,2];Xu, Yue[3];Zhang, Zhiyang[1,2];Lu, Yuanjun[1,2];Li, Run[1,2];Baryshnikov, Glib[4];Li, Chengjie[1,2];Agren, Hans[5];Lu, Hua[6];Li, Qizhao[1,2,3];Xie, Yongshu[1,2]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, Shanghai, Peoples R China;[2]East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Shanghai, Peoples R China;[3]Yantai Nanshan Univ, Coll Chem Engn & Technol, Shandong Prov Engn Res Ctr Novel Funct Polymer Mat, Yantai, Peoples R China;[4]Linkoping Univ, Dept Sci & Technol, Inst Lab Organ Elect, Norrkoping, Sweden;[5]Uppsala Univ, Dept Phys & Astron, Uppsala, Sweden;[6]Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou, Zhejiang, Peoples R China

年份：2026

卷号：21

期号：12

外文期刊名：CHEMISTRY-AN ASIAN JOURNAL

收录：;EI(收录号：20262620982297);WOS:【SCI-EXPANDED(收录号:WOS:001800277500001)】；

基金：This research was financially supported by NSFC (22131005, 22571085), Shanghai Pujiang Program (24PJD024), and Shandong Provincial Natural Science Foundation (ZR2025QC1360). G. B. is thankful for support from the Swedish Research Council (2020-04600) and from the European Union (ERC, LUMOR, 101077649). Views and opinions expressed are however those of the authors only and do not necessarily reflect those of the European Union or the European Research Council Executive Agency. Neither the European Union nor the granting authority can be held responsible for them. The computations were enabled by resources provided by the National Supercomputer Centre (NSC) funded by Linkoping University.

语种：英文

外文关键词：norrole; porphyrinoid; protonation and deprotonation; photothermal conversion

摘要：To extend the absorption spectra of p-phenylene-bridged norroles with the absorption peaks below 700 nm (1 and 2) and probe the photothermal applications in the near-infrared region, cyclization of thiaheptapyrrin (3) afforded a p-phenylene-bridged norrole armed with a thiatetrapyrrin side chain (4) in a 52% yield. Compared to 1 and 2, 4 demonstrates a much narrower HOMO-LUMO gap and considerably red-shifted absorption spectrum tailing to ca. 1150 nm, which may be related to its extended molecular structure. Interestingly, the absorption spectra of both 3 and 4 can be considerably intensified and red-shifted into the near-infrared II region upon protonation and deprotonation. On this basis, photothermal conversion behavior was investigated by irradiating 20 & micro;M solutions with a 1064 nm laser for 10 min. Thus, 3 and 4 exhibited high photothermal conversion efficiencies (PCEs) of 64.5% and 58.9% with temperatures rising to 48.5 degrees C and 36.0 degrees C, respectively. Notably, under identical illumination conditions, protonated and deprotonated forms of 3 demonstrated higher temperature rise to 73.8 degrees C and 77.7 degrees C, respectively. Meanwhile, 4 also shows similar behavior upon protonation and deprotonation. This work provides insights into designing NIR-II photothermal agents by synthesizing long chain oligopyrrins and p-phenylene-bridged norroles in combination with supramolecular means like protonation and deprotonation.