65283-60-5Relevant academic research and scientific papers
A coumarin-based chiral fluorescence sensor for the highly enantioselective recognition of phenylalaninol
Jiao, Jiemin,Liu, Xunhua,Mao, Xuerong,Li, Junfeng,Cheng, Yixiang,Zhu, Chengjian
, p. 317 - 322 (2013)
A chiral host L1 incorporating (S)-BINOL and substituted coumarin moieties was synthesized via a nucleophilic addition-elimination reaction, and ligand L2 could be obtained by the reduction reaction of the imine-based L1 with NaBH 4. The fluorescence responses of chiral compounds L1 and L2 on (l)-/(d)-phenylalaninol were investigated by fluorescence spectra. The fluorescence intensity of L1 in cooperation with (l)-/(d)-phenylalaninol shows a gradual enhancement upon addition of (l)-/(d)-phenylalaninol and keeps a nearly linear correlation with the concentration molar ratios from 1:10 to 1:180. Stoichiometries and association constants of L1 with (l)-/(d)-phenylalaninol were calculated. The results indicate that chiral sensor L1 can exhibit a remarkable "turn-on" fluorescence enhancement response and excellent enantioselective behaviour for (l)-phenylalaninol by direct visual observation at low concentration, and the value of the enantiomeric fluorescence difference ratio (ef) is 3.07. On the contrary, no obvious fluorescence response and enantioselective recognition effect can be detected for L2 towards either (l)-/(d)-phenylalaninol.
Chiral nematic organo-siloxane oligopodes based on an axially chiral binaphthalene core
Schubert, Christopher P. J.,Tamba, M. Gabriela,Mehl, Georg H.
, p. 6851 - 6853 (2012)
The synthesis of a novel class of organosiloxane oligopodes, based on an axially chiral binaphthalene core is described and their mesogenic properties are fully characterised. The Royal Society of Chemistry 2012.
A fluorescence sensor based on chiral polymer for highly enantioselective recognition of phenylalaninol
Meng, Jie,Wei, Guo,Huang, Xiaobo,Dong, Yu,Cheng, Yixiang,Zhu, Chengjian
, p. 363 - 367 (2011)
The chiral polymer P-1 incorporating (S)-2,2′-binaphthol (BINOL) and (S)-2,2′-binaphthyldiamine (BINAM) moieties in the main chain of the polymer backbone was synthesized by the polymerization of (S)-6,6′- dibutyl-3,3′-diformyl-2,2′-binaphthol (S-M-1) with (S)-2,2′-binaphthyldiamine (S-M-2) via nucleophilic addition-elimination reaction, and the chiral polymer P-2 could be obtained by the reduction reaction of P-1 with NaBH4. The fluorescence intensity of the chiral polymer P-1 exhibits gradual enhancement upon addition of (d)- or (l)-phenylalaninol and keeps nearly a linear correlation with the concentration molar ratios of (d)- or (l)-phenylalaninol. The value of enantiomeric fluorescence difference ratio (ef) is 6.85 for the chiral polymer on (d)-phenylalaninol. On the contrary, the chiral polymer P-2 shows no obvious fluorescence response toward either (d)- or (l)-phenylalaninol.
A chiral perazamacrocyclic fluorescent sensor for cascade recognition of Cu(II) and the unmodified α-amino acids in protic solutions
Yang, Xia,Liu, Xuechao,Shen, Kang,Zhu, Chengjian,Cheng, Yixiang
, p. 3510 - 3513 (2011)
A novel chiral Perazamacrocyclic fluorescent sensor (1) was designed and synthesized. It can serve as a fluorescent turn-off sensor with high selectivity toward Cu(II) among 14 metal ions. Furthermore, though 1 exhibits no enantioselectivity, after adding Cu(II), the in situ generated Cu(II)-containing complex of 1 (Cu(II)-1) can exhibit remarkable fluorescent enhancement responses and considerable enantioselectivities toward unmodified α-amino acids in protic solutions via a ligand displacement mechanism; i.e. a cascade recognition of Cu(II) and unmodified α-amino acids has been achieved.
Synthesis and fluorescent properties of a chiral conjugated polymer based on (S)-2,2′-binaphtho-20-crown-6
Huang, Hui,Miao, Qian,Kang, Yixiong,Huang, Xiaobo,Xu, Jinqian,Cheng, Yixiang
, p. 1116 - 1124 (2008)
Linear conjugated polymer was obtained by the polymerization of 2,3-dibutoxy-1,4-diethynylnaphthalene (M-l) and (S)-5,5′-dibromo-6, 6′-dibutyl-2,2′-binaphtho-20-crown-6 (S-M-2) via Pd-catalyzed Sonogashira reaction. The conjugated polymer shows strong green-blue fluorescence due to the extended Π-electronic structure between the chiral repeating unit (S)-6,6′-dibutyl-2,2′-binaphtho-20-crown-6 and the conjugated linker 2,3-dibutoxynaphthyl group via acetylene bridge. The responsive properties of the chiral polymer on K+, Pb2+, Hg2+, and AsIII were investigated by fluorescent spectra. The results show that Hg2+ and AsIII can cause effective fluorescent quenching of the polymer, whereas, K+ and Pb2+ do not produce obvious changes in the polymer fluorescence. The obvious fluorescent influence shows that the 2,2′-binaphtho-20-crown-6 moiety plays an important role in fluorescent recognition for Hg2+ and AsIII due to the effective photoinduced electron transfer (PET) and charge transfer (PCT) between the conjugated polymer backbone and receptor species.
Rationally designed axially chiral diarylethene switches with high helical twisting power
Li, Yannian,Wang, Mengfei,Wang, Hao,Urbas, Augustine,Li, Quan
, p. 16286 - 16292 (2014)
Three rationally designed axially chiral diaryle-thene switches were synthesized and their application as chiral dopants for phototunable cholesteric liquid crystal devices was investigated. Design of these molecules was based on the combination of photoc
Relationships between main-chain chirality and photophysical properties in chiral conjugated polymers
Zheng, Chao,An, Zhongfu,Nakai, Yosuke,Tsuboi, Taiju,Wang, Yang,Shi, Huifang,Chen, Runfeng,Li, Huanhuan,Ji, Yimu,Li, Junfeng,Huang, Wei
, p. 7336 - 7347 (2014)
A series of R- and S-binaphthyl-containing polyfluorenes, bearing different contents and types of axial chirality in the main chain, have been synthesized through Suzuki polycondensation to investigate the influence of the covalently incorporated chirality on the photophysical properties of chiral conjugated polymers. The experimental measurements obtained by UV-Vis and photoluminescence (PL) spectroscopy, cyclic voltammetry, and circular dichroism spectroscopy reveal that the chiral copolymers possess high thermostability, high luminescence efficiency, reversible electrochemical properties, and intrachain transferred dichroism. Surprisingly, the R-chiral polymers exhibit better spectral thermostability, stronger suppressing ability upon the β-phase formation of the main-chain, and higher PL quantum efficiency than S-chiral polymers in solid films. The theoretical insights obtained by either ab initio density functional theory (DFT) calculations or molecular dynamics (MD) simulations suggest that these differences probably resulted from the more planar chain conformation of S-chiral polymers, which leads to stronger interchain interaction and an increased tendency to form inefficient and unstable excimers or quenchers. The different effects of enantiomers on the photophysical properties of chiral conjugated polymers may provide an import update in the understanding of chiro-optics. This journal is the Partner Organisations 2014.
Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases
Yu, Jeong Jae,Ryoo, Jae Jeong
, p. 587 - 596 (2022/01/20)
Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative
Irradiation-Wavelength Directing Circularly Polarized Luminescence in Self-Organized Helical Superstructures Enabled by Hydrogen-Bonded Chiral Fluorescent Molecular Switches
He, Yanrong,Zhang, Shu,Bisoyi, Hari Krishna,Qiao, Jinghui,Chen, Hong,Gao, JingJing,Guo, Jinbao,Li, Quan
supporting information, p. 27158 - 27163 (2021/10/25)
Two light-driven chiral fluorescent molecular switches, (R,S,R)-switch 1 and (R,S,R)-switch 2, are prepared by means of hydrogen-bonded (H-bonded) assembly of a photoresponsive (S) chiral fluorescent molecule, respectively with a cyano substitution at different positions as an H-bond acceptor and an opposite (R) chiral molecule as an H-bond donor. The resulting two switches exhibit tunable and reversible Z/E photoisomerization irradiated with 450 nm blue and 365 nm UV light. When doped into an achiral liquid crystal, both switches are found to be able to form a CPL tunable luminescent helical superstructure. In contrast to the tunable CPL characteristics of the system incorporating switch 2, exposure of the system incorporating switch 1 to 365 nm and 450 nm radiation can lead to controllable different photostationary CPL behavior, including switching-off and polarization inversion. In addition, optical information coding is demonstrated using the system containing switch 1.
Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction
Chen, Yuan,Fang, Siqiang,Pan, Jianke,Ren, Xiaoyu,Tan, Jian-Ping,Wang, Tianli,Zhang, Hongkui
supporting information, p. 14921 - 14930 (2021/05/10)
A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.
