- Molecular recognition of aliphatic diamines by 3,3′- di(trifluoroacetyl)-1,1′-bi-2-naphthol
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The fluorescent responses of 3,3′-di(trifluoroacetyl)-1,1′-bi- 2-naphthol toward a variety of amines have been studied. It was found that the aliphatic primary 1,2- and 1,5-diamines can greatly enhance the fluorescence of this compound, but under the same conditions, primary, secondary, and tertiary monoamines cannot turn on the fluorescence of this compound. In addition, this compound was shown to be an enantioselective and diastereoselective fluorescent sensor for chiral diamines. UV absorption and NMR spectroscopic methods have been used to study the interaction of the sensor with amines. These studies have demonstrated that the intramolecular OH···O=C hydrogen bonding of the sensor is important for both the reactivity of its trifluoroacetyl group with the amines and its fluorescent responses. The interaction of both of the two amine groups of a diamine molecule with the sensor is essential for the observed fluorescent sensitivity and selectivity.
- Yu, Shanshan,Plunkett, Winston,Kim, Michael,Wu, Elaine,Sabat, Michal,Pu, Lin
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Read Online
- Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol
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The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.
- Brégent, Thibaud,Bouillon, Jean-Philippe,Poisson, Thomas
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supporting information
p. 13966 - 13970
(2021/08/25)
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- Synthesis of (±)-3,3′-diphenyl-2,2′-binaphthol via different routes using Pd and Ni as catalyst respectively
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3,3′-Biphenyl-2,2′-binaphthols (BINOLs) are precursors of phosphoric acids that are widely used as ligands and catalysts in organic reactions. In this report, two routes for the synthesis of (±)-3,3′-diphenyl BINOLs via (±)-3,3′ bis-halogenated BINOLs int
- Fu, Zhengjiang,Cao, Xihan,Hao, Guangguo,Shi, Quanqing,Cai, Hu
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p. 831 - 836
(2020/09/09)
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- 1, 1'-bi-2-naphthol derivative and application thereof as fluorescent dye for aqueous coating
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The invention relates to a 1, 1'-bi-2-naphthol derivative and an application thereof as fluorescent dye for aqueous coating, the 1, 1'-bi-2-naphthol derivative is a compound shown in a first formula.The 1, 1'-bi-2-naphthol derivative can be used as fluore
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Paragraph 0031-0035
(2019/06/27)
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- BINOL derivatives with aggression-induced emission
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As fluorescent probes, the small Stokes shift and ACQ effect limit the application of BINOL derivatives. Herein, a new series of BINOL derivatives were synthesized which could be turned from ACQ to AIE fluorophores by changing the electron withdrawing group. Among these compounds, BIN-COP exhibits an obvious AIE property with low cytotoxicity. The bioimaging performance indicated that the designed fluorophores could be successfully used for bioimaging.
- Shi, Lei,Li, Kun,Cui, Peng-Cheng,Li, Ling-Ling,Pan, Sheng-Lin,Li, Meng-Yang,Yu, Xiao-Qi
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supporting information
p. 4413 - 4416
(2018/07/25)
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- Strong Aggregation-Induced CPL Response Promoted by Chiral Emissive Nematic Liquid Crystals (N*-LCs)
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In this paper we designed a kind of aggregation-induced emission (AIE) chiral fluorescence emitters (R/S-BINOL-CN enantiomers) in the aggregate state. Chiral emissive nematic liquid crystals (N*-LCs) prepared by doping this kind of AIE-active R/S-BINOL-CN enantiomers into a common achiral nematic liquid crystal (N-LC, E7) can self-assemble as the regularly planar Grandjean texture leading to high luminescence dissymmetry factor (glum) of aggregation-induced circularly polarized luminescence (AI-CPL) signal up to 0.41, which can be attributed to dipolar interactions from polar cyano groups and π–π interactions between binaphthyl moiety of the dopant R/S-BINOL-CN and biphenyl group of the host molecules (E7).
- Li, Xiaojing,Li, Qian,Wang, Yuxiang,Quan, Yiwu,Chen, Dongzhong,Cheng, Yixiang
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p. 12607 - 12612
(2018/08/11)
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- Aggregation-induced CPL response from chiral binaphthyl-based AIE-active polymers via supramolecular self-assembled helical nanowires
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In this paper chiral polymer R-P could be synthesized by click polymerization reaction of (R)-3,3′-diethynyl-2,2′-bis(octyloxy)-1,1′-binaphthalene (R-M-1) and 1,2-bis(4-azidophenyl)-1,2-diphenylethene (M-2), and S-P was obtained by click polymerization re
- Ma, Jing,Wang, Yuxiang,Li, Xiaojing,Yang, Lan,Quan, Yiwu,Cheng, Yixiang
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p. 184 - 189
(2018/04/14)
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- The amplified circularly polarized luminescence emission response of chiral 1,1′-binaphthol-based polymers via Zn(II)-coordination fluorescence enhancement
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Two kinds of chiral 1,1′-binaphthol (BINOL)-based polymer enantiomers were designed and synthesized by the polymerization of 5,5′-((2,2′-bis (octyloxy)-[1,1′-binaphthalene]-3,3′-diyl)bis(ethyne-2,1-diyl))bis(2-hydroxybenzaldehyde) (M1) with alkyl diamine (M2) via nucleophilic addition–elimination reaction. The resulting chiral polymers can exhibit mirror image cotton effects either in the absence or in the presence of Zn2+ ion. Almost no fluorescence or circularly polarized luminescence (CPL) emission could be observed for two chiral BINOL-based polymer enantiomers in the absence of Zn2+. Interestingly, the chiral polymers can show strong fluorescence and CPL response signals upon the addition of Zn2+, which can be attributed to Zn2+-coordination fluorescence enhancement effect. This work can develop a new strategy on the design of the novel CPL materials via metal-coordination reaction.
- Meng, Fandian,Li, Fei,Yang, Lan,Wang, Yuxiang,Quan, Yiwu,Cheng, Yixiang
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p. 1282 - 1288
(2018/04/14)
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- ESIPT-based ratiometric probe for Zn2+ detection based on BINOL framework
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A ratiometric BINOL-based fluorescent probe for Zn2+ detection was rationally designed and synthesized. Based on the excited-state intramolecular proton transfer (ESIPT) mechanisms, the probe exhibited a significant variation on emission wavele
- Zhang, Kewei,Wu, Shengying,Qu, Dahui,Wang, Limin
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supporting information
p. 1133 - 1137
(2016/03/09)
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- Compound boranil based on bi bisnaphthol of the framework and its preparation and use
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The invention provides a series of Boranil compounds based on 1,1'-binaphthol parents, a preparation method of the compounds, and application of the compounds on detection of fluorine ions. The compounds meet one of the following general formulas, X is on
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Paragraph 0065; 0066
(2016/10/24)
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- A trivalent iron ion fluorescent probe compound, and its preparation and use
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The invention relates to a ferric fluorescent probe compound as well as a preparation method and application thereof. The ferric fluorescent probe compound has the structure in formula I in the specification. The preparation method comprises the following steps: mixing rhodamine B with anhydrous ethanediamine and refluxing in ethyl alcohol to prepare amide of rhodamine; protecting hydroxyl of binaphthol by chloromethyl methyl ether, reacting with N,N-dimethylformamide under the action of butyl lithium, and removing methyl of methyl ether by hydrochloric acid to obtain binaphthol with aldehyde group; finally refluxing the amide of rhodamine and the binaphthol with aldehyde group in ethyl alcohol and washing to obtain the pure ferric fluorescent probe compound. The probe compound has favorable selectivity and sensitivity for the ferric ions, is simple to treat before sample detection and free of causing toxicity to cells, and is used for detecting the ferric ions in the water environment or the biological cells.
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Paragraph 0047; 0049
(2017/03/08)
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- A simple complex: ‘on–off–on’ colorimetric and ratiometric fluorescence response towards fluoride ions and its solid state optical properties
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A simple 1,1′-bi-2-naphthol (1,1′-BINOL) boron complex has been rationally designed and synthesized, the structure of which was confirmed by single crystal X-ray diffraction analysis. Furthermore, the complex exhibited turn-on fluorescence for fluoride ions with high selectivity and sensitivity. The recognition mechanism for promoting was determined by 1H, 19F and 11B NMR titrations, which indicated that both the photo-induced electron-transfer (PET) and the intramolecular charge transfer (ICT) effects were functionalized. In addition, the complex showed strong solid-state fluorescence, and the emission spectrum and quantum efficiency (ΦF) of the solid powders were also measured.
- Wu, Shengying,Chen, Zhijun,Zhang, Kewei,Hong, Gang,Zhao, Guosheng,Wang, Limin
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supporting information
p. 1390 - 1395
(2018/03/29)
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- Chiral polyethers derived from BINOL and ECH as highly enantioselective and efficient catalysts for the borane reduction of prochiral ketones
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Two novel polyethers derived from BINOL were synthesized and used to induce the enantioselective borane reduction of prochiral ketones. The polyethers gave the expected secondary alcohols with up to 98% yields and over 99% ee values. The recovered polyethers could be reused for many times to induce the enantioselective reduction of prochiral ketones without losing their enantioselective induction ability.
- Zhang, An-Lin,Yu, Zeng-Da,Yang, Li-Wen,Yang, Nian-Fa,Peng, Dan
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p. 407 - 412
(2015/01/30)
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- CPL emission of chiral BINOL-based polymers via chiral transfer of the conjugated chain backbone structure
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Two chiral BINOL-based polymer enantiomers R-P and S-P incorporating phenothiazine moieties in the main chain backbone can exhibit mirror image Cotton effects and emit green color circularly polarized luminescence (CPL), which can be attributed to chiral transfer of binaphthyl to chromophore phenothiazine moieties via the conjugated polymer chain backbone.
- Li, Fei,Wang, Yuxiang,Sheng, Yuan,Wei, Guo,Cheng, Yixiang,Zhu, Chengjian
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p. 105851 - 105854
(2015/12/30)
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- A novel Cr3+ turn-on probe based on naphthalimide and BINOL framework
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Naphthalimide and BINOL framework based fluorescent probe NP-B was rationally designed and synthesized. NP-B exhibited 'turn-on' fluorescence for Cr3+ and high selectivity over other metal ions. 1:1 binding mode between NP-B and Cr3+ was proposed and the mode was verified through MALDI-TOF mass spectrum. The detection limit was calculated to be 0.20 μM, which indicated the good sensitivity for Cr3+.
- Wu, Shengying,Zhang, Kewei,Wang, Yefeng,Mao, Dan,Liu, Xin,Yu, Jianjun,Wang, Limin
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p. 351 - 353
(2014/01/06)
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- Synthesis, properties, and structures of functionalized peri -xanthenoxanthene
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Three types of alkylated peri-xanthenoxanthene (PXX) have been synthesized employing efficient synthetic routes. These heteroaromatic compounds exhibited different electronic and crystal structures according to UV-vis spectra, electrochemical measurements, and X-ray structural analyses. Among them, 1,7-DOPXX has been demonstrated as an active material for organic field-effect transistors with promising mobility and a high on/off ratio simultaneously.
- Lv, Na,Xie, Meilan,Gu, Weibing,Ruan, Huanyang,Qiu, Song,Zhou, Chunshan,Cui, Zheng
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supporting information
p. 2382 - 2385
(2013/07/04)
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- METHODS OF MAKING DIASTEREOMERIC ORGANIC COMPOUNDS
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Disclosed is a process for making diastereomeric compound of the formula (I): wherein m, n and R1 to R4 are as defined herein. The process of the invention provides the compound of formula (I) in high yield and substantially free of
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Page/Page column 32-33
(2012/07/13)
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- A facile method for the rapid and selective deprotection of methoxymethyl (MOM) ethers
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We describe a rapid and efficient method for selective deprotection of methoxymethyl (MOM) ethers using ZnBr2 and n-PrSH, which completely removed MOM from diverse MOM ethers of primary, secondary, and tertiary alcohols or phenol derivatives. The deprotection takes less than ten minutes with both high yield and selectivity in the presence of other protecting groups. In addition, the rapid deprotection of MOM ethers of tertiary hydroxyls in high yield with no epimerization allows MOM to be a suitable protecting group for tertiary alcohols.
- Han, Jae Hyun,Kwon, Young Eun,Sohn, Jeong-Hun,Ryu, Do Hyun
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experimental part
p. 1673 - 1677
(2010/04/04)
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- Chiral Ti(IV) complexes of hexadentate Schiff bases as precatalysts for aldehyde allylation: unusual additive effect of trimethylsilyl chloride
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Chiral dinuclear titanium(IV) complexes have been found to be more effective catalysts for the asymmetric allylation of p-nitrobenzaldehyde than their mononuclear analogues. The addition of trimethylsilyl chloride to the reaction mixture decreases the rate of the background reaction and increases the yield of the reaction catalysed by the dinuclear complex.
- Belokon, Yuri N.,Chusov, Denis,Borkin, Dmitry A.,Yashkina, Lidia V.,Bolotov, Pavel,Skrupskaya, Tatiana,North, Michael
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p. 459 - 466
(2008/09/19)
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- CATALYST FOR ASYMMETRIC SYNTHESIS, LIGAND FOR USE THEREIN, AND PROCESS FOR PRODUCING OPTICALLY ACTIVE COMPOUND THROUGH ASYMMETRIC SYNTHESIS REACTION USING THEM
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Compounds represented by the following general formula (1a) or (1b). A complex comprising a center metal of rhodium and a compound represented by the following general formula (1a) or (1b) as a ligand. A catalyst for optically active beta-substituted carbonyl compound synthesis and catalyst for asymmetric 1, 2 addition reaction being composed of the complex. A method of production of an optically active beta-aryl compound from an alpha, beta-unsaturated compound and an aryl-boronic acid derivative and method of production of an optically active aryl alcohol compound from an aldehyde compound and aryl boronic acid derivatives using the catalyst. A complex comprising a center metal of palladium and a compound represented by the following general formula (1a) or (1b) as a ligand. A catalyst for asymmetric allylic substitution reaction being composed of the complex. A method of production of an optically active dialkyl (1,3-disubstituted propeny)malonate compound from a 1,3- disubstituted ally acetate compound and a dialkyl malonate and method of production of an optically active allylamine compound from a 1,3-disubstituted ally acetate compound and an amine compound. The compounds have not only the versatility of being usable in the synthesis of wide-ranging optically active aryl compounds but also the selectivity and reactivity permitting synthesis with high yield within a short period of time under industrially advantageous mild conditions.
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Page/Page column 19
(2008/06/13)
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- Synthesis of new bifunctional BINOL derivatives
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A series of new 3,3′-disubstituted BINOL derivatives have been synthesised. In a preliminary study, the asymmetric induction of these ligands was investigated in the addition of diethyl zinc to benzaldehyde in the absence of Ti(Oi-Pr)4. This showed different enantioselectivity and activity from those of the unsubstituted BINOL.
- Zhang, Yi-Li,Fan, Qing-Hua
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p. 778 - 779
(2007/10/03)
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- Asymmetric allylboration of aldehydes and ketones using 3,3′-disubstitutedbinaphthol-modified boronates
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Allylboronates derived from 3,3′-disubstituted 2,2′-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness.
- Wu, T. Robert,Shen, Lixin,Chong, J. Michael
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p. 2701 - 2704
(2007/10/03)
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- Compositions and methods for selectively binding amines or amino acid enantiomers over their counter-enantiomers
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Naphthyl crown ether ligand molecules containing at least two naphthyl groups that are covalently bonded to suitable solid supports and coated by hydrophobic organic solvents are disclosed. These compositions and associated methods are characterized by selectivity of desired amine or amino acid enantiomers over their counter-enantiomers and derivatives. The composition preferably has an α-value greater than or equal to 4. This allows for the separation of such enantiomers with nonchromatographic resin bed separations of three separation stages or less.
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Page column 10; 11
(2010/11/30)
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- Axially dissymmetric binaphthyldiimine chiral Salen-type ligands for catalytic asymmetric addition of diethylzinc to aldehyde
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The axially dissymmetric chiral Schiff base ligand 10, prepared by the reaction of (R)-(+)-1,1′-binaphthyl-2,2′-diamine with (R)-(+)-2,2′-dihydroxy-[1,1′]-binaphthalenyl-3-carbaldehyde, is a fairly effective chiral ligand for the catalytic asymmetric addition reaction of diethylzinc to aldehydes.
- Shi, Min,Wang, Chun-Jiang
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p. 2161 - 2166
(2007/10/03)
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- Developments in the simmons-smith-mediated epoxidation reaction
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The reaction between Et2Zn, ClCH2I, sulfide, and aldehyde furnishes terminal epoxides in high yields. The reaction occurs via a zinc carbenoid, which reacts with the sulfide to furnish an ylide, which in turn reacts with the aldehyde to give the epoxide. Chiral ligands capable of chelation to zinc [1,2-amino alcohols, amino acids, bis(oxazolines), taddols] were examined, but only low enantioselectivity was observed (up to 11% ee). A number of chiral sulfides were also examined, but again only low enantioselectivity was observed (up to 16% ee). However, linking a sulfide to a metal capable of chelation to zinc [a bis(oxazoline) bearing a sulfide at the 5 position] produced a reagent that gave up to 54% ee in the epoxidation process. The same system was applied to the preparation of terminal aziridines from imines. The optimum group on nitrogen was a sulfonyl group, although groups capable of chelation of zinc (o-methoxyphenyl) were also effective. Attempts to render the aziridination process asymmetric by using the above strategy were less successful (up to 19% ee). WILEY-VCH Verlag GmbH 2002.
- Aggarwal, Varinder K.,Coogan, Michael P.,Stenson, Rachel A.,Jones, Raymond V. H.,Fieldhouse, Robin,Blacker, John
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p. 319 - 326
(2007/10/03)
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- Catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile promoted by gallium heterobimetallic multifunctional complexes
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The catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile (4-methoxyphenol) is described for the first time herein. This reaction was first found to be promoted by (R)-GaLB (Ga = gallium, L = lithium, B = (R)-BINOL), giving a variety of epoxide opening products in good to high ee (67-93% ee). However, chemical yield was only modest (yield 31-75%), despite the use of more than 20 mol % GaLB. This was due to the undesired ligand exchange between BINOL and 4-methoxyphenol, which resulted in the decomplexation of GaLB. Application of various known chiral ligands such as 6,6'-bis((triethylsilyl)ethynyl)-BINOL and H8-BINOL were examined, but satisfactory results were not obtained. To overcome this problem a novel linked-BINOL containing coordinative oxygen atom in the linker has been developed. By linking two BINOL units in GaLB, the stability of the Ga-complex was greatly improved. Using 3-10 mol % (R,R)-Ga-Li-linked- BINOL complex, a variety of epoxide opening reactions were found to proceed smoothly, affording products in analogous ee (66-96% ee) and in much higher yield (yield 67-94%) compared to (R)-GaLB. The structure of the LiCl free Ga- Li-linked-BINOL complex was elucidated by X-ray analysis. This is the first X-ray data for an asymmetric catalyst containing gallium. The possible mechanism of the entitled reaction is also discussed, based on the X-ray structure of the Ga-complex.
- Matsunaga,Das,Roels,Vogl,Yamamoto,Iida,Yamaguchi,Shibasaki
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p. 2252 - 2260
(2007/10/03)
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- Asymmetric Simmons-Smith Cyclopropanation of E-Allylic Alcohols Using 1,1'-Bi-2-naphthol-3,3'-dicarboxamide as a Chiral Auxiliary
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N,N,N',N'-Tetraethyl-1,1'-bi-naphthol-3,3'-dicarboxamide (1b) was found to be an effective chiral auxiliary for asymmetric Simmons-Smith cyclopropanation and high enantioselectivity greater than 85percent ee was achieved in the reaction of E-allylic alcohols.
- Kitajima, Hiroshi,Aoki, Yuko,Ito, Katsuji,Katsuki, Tsutomu
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p. 1113 - 1114
(2007/10/03)
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- Host- Guest Complexation. 22. Reciprocal Chiral Recognition between Amino Acids and Dilocular Systems
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The direction of configurational bias and the extent of chiral recognition have been determined for complexation between seven amino acid perchlorate guests and four macrocyclic polyether hosts containing chiral elements.In solution experiments, racemic g
- Peacock, Stephen S.,Walba, David M.,Gaeta, Fred C. A.,Helgeson, Roger C.,Cram, Donald J.
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p. 2043 - 2052
(2007/10/02)
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