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Article: Benzo-Extended Heli(aminoborane)s: Inner Rim BN-Doped Helical Molecular Carbons with Remarkable Chiroptical Properties

TitleBenzo-Extended Heli(aminoborane)s: Inner Rim BN-Doped Helical Molecular Carbons with Remarkable Chiroptical Properties
Authors
Issue Date5-Aug-2024
PublisherAmerican 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 Identifierhttp://hdl.handle.net/10722/348759
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489

 

DC FieldValueLanguage
dc.contributor.authorYu, Yang-
dc.contributor.authorWang, Chang-
dc.contributor.authorHung, Faan Fung-
dc.contributor.authorChen, Chen-
dc.contributor.authorPan, Ding-
dc.contributor.authorChe, Chi Ming-
dc.contributor.authorLiu, Junzhi-
dc.date.accessioned2024-10-15T00:30:38Z-
dc.date.available2024-10-15T00:30:38Z-
dc.date.issued2024-08-05-
dc.identifier.citationJournal of the American Chemical Society, 2024, v. 146, n. 32, p. 22600-22611-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://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.languageeng-
dc.publisherAmerican Chemical Society-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleBenzo-Extended Heli(aminoborane)s: Inner Rim BN-Doped Helical Molecular Carbons with Remarkable Chiroptical Properties-
dc.typeArticle-
dc.identifier.doi10.1021/jacs.4c06997-
dc.identifier.pmid39101597-
dc.identifier.scopuseid_2-s2.0-85200562960-
dc.identifier.volume146-
dc.identifier.issue32-
dc.identifier.spage22600-
dc.identifier.epage22611-
dc.identifier.eissn1520-5126-
dc.identifier.issnl0002-7863-

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