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- Publisher Website: 10.1021/jacs.4c06997
- Scopus: eid_2-s2.0-85200562960
- PMID: 39101597
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Article: Benzo-Extended Heli(aminoborane)s: Inner Rim BN-Doped Helical Molecular Carbons with Remarkable Chiroptical Properties
Title | Benzo-Extended Heli(aminoborane)s: Inner Rim BN-Doped Helical Molecular Carbons with Remarkable Chiroptical Properties |
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Authors | |
Issue Date | 5-Aug-2024 |
Publisher | American Chemical Society |
Citation | Journal of the American Chemical Society, 2024, v. 146, n. 32, p. 22600-22611 How to Cite? |
Abstract | Atomically precise synthesis of three-dimensional boron–nitrogen (BN)-based helical structures constitutes an undeveloped field with challenges in synthetic chemistry. Herein, we synthesized and comprehensively characterized a new class of helical molecular carbons, named benzo-extended [n]heli(aminoborane)s ([n]HABs), in which the helical structures consisted of n = 8 and n = 10 ortho-condensed conjugated rings with alternating BN atoms at the inner rims. X-ray crystallographic analysis, photophysical studies, and density functional theory calculations revealed the unique characteristics of this novel [n]HAB system. Owing to the high enantiomerization energy barriers, the optical resolution of [8]HAB and [10]HAB was achieved with chiral high-performance liquid chromatography. The isolated enantiomers of [10]HAB exhibited record absorption and luminescence dissymmetry factors (|gabs|=0.061; |glum|=0.048), and boosted CPL brightness up to 292 M–1 cm–1, surpassing most helicene derivatives, demonstrating that the introduction of BN atoms into the inner positions of helicenes can increase both the |gabs| and |glum| values. |
Persistent Identifier | http://hdl.handle.net/10722/348759 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
DC Field | Value | Language |
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dc.contributor.author | Yu, Yang | - |
dc.contributor.author | Wang, Chang | - |
dc.contributor.author | Hung, Faan Fung | - |
dc.contributor.author | Chen, Chen | - |
dc.contributor.author | Pan, Ding | - |
dc.contributor.author | Che, Chi Ming | - |
dc.contributor.author | Liu, Junzhi | - |
dc.date.accessioned | 2024-10-15T00:30:38Z | - |
dc.date.available | 2024-10-15T00:30:38Z | - |
dc.date.issued | 2024-08-05 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2024, v. 146, n. 32, p. 22600-22611 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/348759 | - |
dc.description.abstract | <p>Atomically precise synthesis of three-dimensional boron–nitrogen (BN)-based helical structures constitutes an undeveloped field with challenges in synthetic chemistry. Herein, we synthesized and comprehensively characterized a new class of helical molecular carbons, named benzo-extended [n]heli(aminoborane)s (<strong>[n]HAB</strong>s), in which the helical structures consisted of <em>n</em> = 8 and <em>n</em> = 10 <em>ortho</em>-condensed conjugated rings with alternating BN atoms at the inner rims. X-ray crystallographic analysis, photophysical studies, and density functional theory calculations revealed the unique characteristics of this novel <strong>[n]HAB</strong> system. Owing to the high enantiomerization energy barriers, the optical resolution of <strong>[8]HAB</strong> and <strong>[10]HAB</strong> was achieved with chiral high-performance liquid chromatography. The isolated enantiomers of <strong>[10]HAB</strong> exhibited record absorption and luminescence dissymmetry factors (|<em>g</em><sub>abs</sub>|=0.061; |<em>g</em><sub>lum</sub>|=0.048), and boosted CPL brightness up to 292 M<sup>–1</sup> cm<sup>–1</sup>, surpassing most helicene derivatives, demonstrating that the introduction of BN atoms into the inner positions of helicenes can increase both the |<em>g</em><sub>abs</sub>| and |<em>g</em><sub>lum</sub>| values.</p> | - |
dc.language | eng | - |
dc.publisher | American Chemical Society | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Benzo-Extended Heli(aminoborane)s: Inner Rim BN-Doped Helical Molecular Carbons with Remarkable Chiroptical Properties | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/jacs.4c06997 | - |
dc.identifier.pmid | 39101597 | - |
dc.identifier.scopus | eid_2-s2.0-85200562960 | - |
dc.identifier.volume | 146 | - |
dc.identifier.issue | 32 | - |
dc.identifier.spage | 22600 | - |
dc.identifier.epage | 22611 | - |
dc.identifier.eissn | 1520-5126 | - |
dc.identifier.issnl | 0002-7863 | - |