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在温和条件下获得具有延迟荧光和聚集诱导发光的四配位硼掺杂多环芳烃。

Access to tetracoordinate boron-doped polycyclic aromatic hydrocarbons with delayed fluorescence and aggregation-induced emission under mild conditions.

作者信息

Jiang Long, Wang Yu, Tan Dehui, Chen Xiaobin, Ma Tinghao, Zhang Baoliang, Yang Deng-Tao

机构信息

School of Chemistry and Chemical Engineering, Northwestern Polytechnical University Xi'an Shanxi 710072 China

School of Chemistry and Chemical Engineering, Beijing Institute of Technology Beijing 100081 China.

出版信息

Chem Sci. 2022 Apr 29;13(19):5597-5605. doi: 10.1039/d2sc01722a. eCollection 2022 May 18.

DOI:10.1039/d2sc01722a
PMID:35694347
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9116330/
Abstract

Boron-doped polycyclic aromatic hydrocarbons (PAHs) have attracted ongoing attention in the field of optoelectronic materials due to their unique optical and redox properties. To investigate the effect of tetracoordinate boron in PAHs bearing N-heterocycles (indole and carbazole), a facile approach to four-coordinate boron-doped PAHs was developed, which does not require elevated temperature and pre-synthesized functionalized boron reactants. Five tetracoordinate boron-doped PAHs (NBNN-1-NBNN-5) were synthesized with different functional groups. Two of them (NBNN-1 and NBNN-2) could further undergo oxidative coupling reactions to form fused off-plane tetracoordinate boron-doped PAHs NBNN-1f and NBNN-2f. The investigation of photophysical properties showed that the UV/vis absorption and fluorescence emission are significantly red-shifted compared to those of the three-coordinate boron-doped counterparts. In addition, the emission of NBNN-1-NBNN-3 consisted of prompt fluorescence and delayed fluorescence. The compounds NBNN-1f and NBNN-2f showed aggregation-induced emission.

摘要

硼掺杂的多环芳烃（PAHs）因其独特的光学和氧化还原性质，在光电子材料领域一直备受关注。为了研究四配位硼对含氮杂环（吲哚和咔唑）的多环芳烃的影响，开发了一种简便的合成四配位硼掺杂多环芳烃的方法，该方法无需高温和预先合成的官能化硼反应物。合成了五种具有不同官能团的四配位硼掺杂多环芳烃（NBNN-1-NBNN-5）。其中两种（NBNN-1和NBNN-2）可进一步发生氧化偶联反应，形成稠合的面外四配位硼掺杂多环芳烃NBNN-1f和NBNN-2f。光物理性质研究表明，与三配位硼掺杂的类似物相比，紫外/可见吸收和荧光发射明显红移。此外，NBNN-1-NBNN-3的发射由即时荧光和延迟荧光组成。化合物NBNN-1f和NBNN-2f表现出聚集诱导发光。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/1e9136941e9e/d2sc01722a-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/d871aa845004/d2sc01722a-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/b3cf545ba35d/d2sc01722a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/8cbd5696454c/d2sc01722a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/a71e66cef97a/d2sc01722a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/7c8114a51250/d2sc01722a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/55195286d678/d2sc01722a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/3265f7fbcc9f/d2sc01722a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/1e9136941e9e/d2sc01722a-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/d871aa845004/d2sc01722a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/4b2266bcf6af/d2sc01722a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/b3cf545ba35d/d2sc01722a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/8cbd5696454c/d2sc01722a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/a71e66cef97a/d2sc01722a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/7c8114a51250/d2sc01722a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/55195286d678/d2sc01722a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/3265f7fbcc9f/d2sc01722a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f4df/9116330/1e9136941e9e/d2sc01722a-f6.jpg

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