Cheng Jun, Yang Liuqing, Wang Ruiyao, Wisner James A, Ding Zhifeng, Wang Hong-Bo
Key Laboratory of Optoelectronic Chemical Materials and Devices, Ministry of Education, School of Optoelectronic Materials and Technology, Jianghan University Wuhan Hubei 430056 China
XJTLU Wisdom Lake Academy of Pharmacy, Xi'an Jiaotong-Liverpool University 111 Ren'an Road Suzhou Jiangsu 215123 China.
Chem Sci. 2024 Jul 4;15(31):12291-12300. doi: 10.1039/d4sc03338h. eCollection 2024 Aug 7.
Herein, intensified electrochemiluminescence (ECL) and photoluminescence (PL) supramolecular anion recognition interactions are demonstrated. A bisindolylpyrrole derivative with a structure containing two indole groups and 2-hexyl-pyrrolo[3,4-]pyrrole-1,3(2,5)-dione, BIPPD, was designed and synthesized to induce the enhanced ECL and PL emission based on hydrogen bonding interactions with the dihydrogen phosphate anion. Remarkably, the ECL quantum efficiency and PL quantum yield were discovered to increase up to 5.5-fold and 1.5-fold, respectively, this anion coordination. Dopant PF was found not to form hydrogen bonds, while HSO doping does slightly with the receptor molecule. There was no enhancement in either ECL or PL in both scenarios, revealing great recognition selectivity of the synthesized BIPPD. Mechanistic studies H NMR, ECL, and PL spectra illustrated that the ECL processes varied in the presence and absence of HPO doping, thus leading to the understanding of enhanced efficiency. The bisindolylpyrrole derivative will find applications in supramolecular and analytical chemistry controlled hydrogen bonding interactions.
在此，展示了增强型电化学发光（ECL）和光致发光（PL）超分子阴离子识别相互作用。设计并合成了一种双吲哚基吡咯衍生物，其结构包含两个吲哚基团和2-己基-吡咯并[3,4 - ]吡咯-1,3(2,5)-二酮，即BIPPD，以基于与磷酸二氢根阴离子的氢键相互作用诱导增强的ECL和PL发射。值得注意的是，发现这种阴离子配位使ECL量子效率和PL量子产率分别提高至5.5倍和1.5倍。发现掺杂剂PF不形成氢键，而HSO与受体分子有轻微掺杂。在这两种情况下，ECL和PL均未增强，这表明合成的BIPPD具有很高的识别选择性。机理研究通过1H NMR、ECL和PL光谱表明，在存在和不存在HPO掺杂的情况下，ECL过程有所不同，从而有助于理解效率的提高。这种双吲哚基吡咯衍生物将在基于可控氢键相互作用的超分子和分析化学中找到应用。
