74866-27-6Relevant articles and documents
Molecular design to enhance binaphthyl-based chiroptics using organoboron chemistry in isomeric chiral scaffolds
Chen, Jin-Fa,Chen, Pangkuan,Wang, Nan,Yin, Xiaodong,Zhang, Kai,Zhang, Niu,Zhao, Jingyi,Zheng, Xiaoyan
supporting information, p. 1816 - 1824 (2022/02/17)
Access to high-performance circularly polarized luminescence is highly desired in materials science but it hitherto remains a considerable challenge. We herein present a conceptually universal design strategy to improve the chiral luminescent properties of a series of binaphthyl-based compounds (MeBTT, MeBTB, p-BTT, p-BTB, m-BTT and m-BTB). The binaphthyl skeleton in all cases was π-functionalized either by an electron donor (Ar3N) or acceptor (Ar3B), and correlations of the molecular structures to their photophysical characters were systematically investigated. They all exhibited strong photoluminescence both in solution with quantum efficiency (ΦPL,DCM) up to 100% and as solids (ΦPL,solid = 21-59%). The optical resolution into enantiomers via chiral HPLC was achieved for p-BTT, p-BTB, m-BTT and m-BTB with helically ring-structured binaphthyls. We further unveiled that the sterically more constrained m-BTT and m-BTB exhibit superior chiroptical properties in circularly polarized luminescence (CPL) relative to the isomers p-BTT and p-BTB, evident from the order of magnitude of luminescence dissymmetry factor (|glum|) increasing from 10-4 to 10-3 in solution. Moreover, the double functionalization of the binaphthyl moiety with an electron donor-acceptor charge-transfer system resulted also in an experimentally improved CPL activity, as rationalized by TD-DFT calculations of a key angle (θμ,m) between vectors of the electric and magnetic transition dipole moments in the excited states. The three organoboranes (MeBTB, p-BTB and m-BTB) displayed dual emissions in polar solvents and the low-energy charge transfer bands were demonstrated to be air-sensitive and thermally responsive at elevated temperature. This journal is
New compound and a manufacturing method thereof and a like annular crown ether binaphthayl group having the structure
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Paragraph 0066, (2016/10/27)
PROBLEM TO BE SOLVED: To provide a novel compound including a crown ether-like structure and an optically active binaphthyl group which is expected in the application as an asymmetry recognizing agent and in various applications as various functional materials and to provide a manufacturing method thereof. SOLUTION: The novel compound having a crown ether-like structure and a binaphthyl structure is provided by further derivatizing a binaphthyl derivative in which the 6,6'-positions are replaced with bromines and the 3,3'-positions are replaced with specific substituents, by a specific reaction. COPYRIGHT: (C)2013,JPOandINPIT
Efficient oxidative biaryl coupling reaction of phenol ether derivatives using hypervalent iodine(III) reagents
Tohma, Hirofumi,Morioka, Hironori,Takizawa, Shinobu,Arisawa, Mitsuhiro,Kita, Yasuyuki
, p. 345 - 352 (2007/10/03)
Oxidative biaryl coupling reaction of phenol ether derivatives with the hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), in the presence of BF3·Et2O gave a variety of substituted biphenyl and binaphthyl compounds in high yields. Replacement of PIFA with a more practical polymer-supported hypervalent iodine reagent has also been achieved.
