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Dehui Tan Jiaqi Dong Tinghao Ma Prof. Dr. Qingliang Feng Prof. Dr. Suning Wang Prof. Dr. Deng-Tao Yang 《Angewandte Chemie (International ed. in English)》2023,62(29):e202304711
The incorporation of heteroatoms and/or heptagons as the defects into helicenes expands the variety of chiroptical materials with novel properties. However, it is still challenging to construct novel boron-doped heptagon-containing helicenes with high photoluminescence quantum yields (PLQYs) and narrow full-width-at-half-maximum (FWHM) values. We report an efficient and scalable synthesis of a quadruple helicene 4Cz-NBN with two nitrogen-boron-nitrogen (NBN) units and a double helicene 4Cz-NBN-P1 bearing two NBN-doped heptagons, the latter could be formed via a two-fold Scholl reaction of the former. The helicenes 4Cz-NBN and 4Cz-NBN-P1 exhibit excellent PLQYs up to 99 % and 65 % with narrow FWHM of 24 nm and 22 nm, respectively. The emission wavelengths are tunable via stepwise titration experiments of 4Cz-NBN-P1 toward fluoride, enabling distinguished circularly polarized luminescence (CPL) from green, orange (4Cz-NBN-P1-F1) to yellow (trans/cis-4Cz-NBN-P1-F2) with near-unity PLQYs and broader circular dichroism (CD) ranges. The five structures of the aforementioned four helicenes were confirmed by single crystal X-ray diffraction analysis. This work provides a novel design strategy for construction of non-benzenoid multiple helicenes exhibiting narrow emissions with superior PLQYs. 相似文献
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Lin Yang Dr. Yang-Yang Ju Dr. Miguel A. Medel Dr. Yubin Fu Dr. Hartmut Komber Dr. Evgenia Dmitrieva Dr. Jin-Jiang Zhang Sebastian Obermann Prof. Dr. Araceli G. Campaña Dr. Ji Ma Prof. Dr. Xinliang Feng 《Angewandte Chemie (International ed. in English)》2023,62(4):e202216193
The precision synthesis of helical bilayer nanographenes (NGs) with new topology is of substantial interest because of their exotic physicochemical properties. However, helical bilayer NGs bearing non-hexagonal rings remain synthetically challenging. Here we present the efficient synthesis of the first helical bilayer nonbenzenoid nanographene ( HBNG1 ) from a tailor-made azulene-embedded precursor, which contains a novel [10]helicene backbone with two embedded heptagons. Single-crystal X-ray analysis reveals its highly twisted bilayer geometry with a record small interlayer distance of 3.2 Å among the reported helical bilayer NGs. Notably, the close interlayer distance between the two layers offers intramolecular through-space conjugation as revealed by in situ spectroelectrochemistry studies together with DFT simulations. Furthermore, the chiroptical properties of the P/M enantiomers of HBNG1 are also evaluated by circular dichroism and circularly polarized luminescence. 相似文献
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