- Spiro-bis-benzoxazole diamine and preparation method and application thereof, polyimide and preparation method and application thereof
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The invention belongs to the technical field of macromolecules, and particularly relates to spirobibenzoxazole diamine, a preparation method and application thereof, polyimide and a preparation method and application thereof. According to the present invention, the spiro-bis-benzoxazole diamine is adopted as the monomer to prepare the polyimide, and the spiro structure is introduced into the diamine structure, such that the obtained polyimide has excellent solubility and excellent processability; meanwhile, the polyimide forms a microporous structure, so that the gas permeability of the polyimide is improved.
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Paragraph 0065-0066; 0185-0186
(2021/09/04)
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- Development of C2-Symmetric Chiral Spirocyclic Phase-Transfer Catalysts: Synthesis and Application to Asymmetric Alkylation of Glycinate Schiff Base
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A class of C2-symmetric chiral spirocyclic phase-transfer catalysts based on tetramethyl-1,1′-spirobiindane scaffold was synthesized from commercially available bisphenol A in 12 steps with 22-25% total yields, which features a more rigid and stable backb
- Xu, Changming,Qi, Yinsheng,Yang, Xinshuang,Li, Xiangfan,Li, Zhenpeng,Bai, Lei
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supporting information
p. 2890 - 2894
(2021/05/05)
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- Organic compound and organic electroluminescent device thereof
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The invention provides an organic compound and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials. According to the invention, the organiccompound provided by the invention is obtained by introd
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Paragraph 0132-0134
(2020/11/23)
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- CFA-18: A homochiral metal-organic framework (MOF) constructed from rigid enantiopure bistriazolate linker molecules
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In this work, we introduce the first enantiopure bistriazolate-based metal-organic framework, CFA-18 (Coordination Framework Augsburg-18), built from the R-enantiomer of 7,7,7′,7′-tetramethyl-6,6′,7,7′-tetrahydro-3H,3′H-5,5′-spirobi[indeno[5,6-d]-[1,2,3]triazole] (H2-spirta). The enantiopurity and absolute configuration of the new linker were confirmed by several chiroselective methods. Reacting H2-spirta in hot N,N-dimethylformamide (DMF) with manganese(ii) chloride gave CFA-18 as colorless crystals. The crystal structure with the composition [Mn2Cl2(spirta)(DMF)2] was solved using synchrotron single-crystal X-ray diffraction. CFA-18 shows a framework topology that is closely related to previously reported metal-azolate framework (MAF) structures in which the octahedrally coordinated manganese(ii) ions are triazolate moieties, and the chloride anions form crosslinked one-dimensional helical chains, giving rise to hexagonal channels. In contrast to MAFs crystallizing in the centrosymmetric space group R3, the handedness of the helices found in CFA-18 is strictly uniform, leading to a homochiral framework that crystallizes in the trigonal crystal system within the chiral space group P3121 (no. 152). This journal is
- Bredenk?tter, Bj?rn,Bultinck, Patrick,Herrebout, Wouter,Kanschat, Lisa,Knippen, Katharina,Kraft, Maryana,Sugimoto, Kunihisa,Vermeyen, Tom,Volkmer, Dirk
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p. 15758 - 15768
(2020/11/24)
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- Arylamine-based organic compound and organic light-emitting device thereof (by machine translation)
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The invention provides an arylamine organic compound and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials. The arylamine type organic compound disclosed by the invention adopts tetramethyl spi
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Paragraph 0129-0132
(2020/09/16)
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- Molecular engineering of high-performance nanofiltration membranes from intrinsically microporous poly(ether-ether-ketone)
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Poly(ether-ether-ketone) has received increased attention due to its high thermal and chemical stability, and high performance in various applications. However, it suffers from a semi-crystalline morphology, low fractional free volume, and poor processability, requiring the use of harsh acidic solvents, which leads to undesired sulfonation. In this work, three intrinsically microporous poly(ether-ether-ketones) (iPEEKs), incorporating spirobisindane, Tr?ger's base, and triptycene contorted structures, were developed for organic solvent nanofiltration. Molecular dynamics simulations have assisted the molecular engineering of the polymers and the understanding of the improved membrane performance through the binding energies between solvents and polymers. Application of the design principles of polymers of intrinsic microporosity has led to a paradigm shift with a notable enhancement in both the polymer properties and the subsequently fabricated nanofiltration membranes' performance. The iPEEKs showed excellent solution processability, a high surface area of 205-250 m2 g-1, and excellent thermal stability. Mechanically flexible nanofiltration membranes were prepared from N-methyl-2-pyrrolidone dope solution at iPEEK concentrations of 19-35 wt%. The molecular weight cutoff of the membranes was fine-tuned in the range of 450-845 g mol-1 displaying 2-6 fold higher permeance (3.57-11.09 L m-2 h-1 bar-1) than previous reports. The long-term stabilities were demonstrated by a 7 day continuous cross-flow filtration. This journal is
- Abdulhamid, Mahmoud A.,Akhtar, Faheem Hassan,Ng, Kim Choon,Park, Sang-Hee,Schwingenschl?gl, Udo,Szekely, Gyorgy,Vovusha, Hakkim
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p. 24445 - 24454
(2020/12/21)
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- Aromatic polyimides containing pyridine and spirocyclic units: Preparation, thermal and gas separation properties
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Six polyimides, containing pyridine and spirocyclic units, were successfully synthesized by chemical imidization. Structure-dependent properties such as thermal decomposition temperatures and gas permeabilities of the high-performance polymers were explicitly investigated. Results showed that all polyimide films exhibited good solubility in common organic solvents and non-polar solvents such as chloroform and tetrahydrofuran. The polymers exhibited good thermal stability, all demonstrating thermal decomposition temperatures (Td10%) over 496 °C in nitrogen. Important from a commercial viewpoint, the permeability coefficients of these for the acidic gas CO2 showed an increase over other tested gases by virtue of the basic group pyridine (C–N linkages) in their structures.
- Wang, Shuli,Ma, Shengqi,He, Hongru,Ai, Wenming,Wang, Daming,Zhao, Xiaogang,Chen, Chunhai
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p. 199 - 208
(2019/03/14)
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- Atroposelective Phosphoric Acid Catalyzed Three-Component Cascade Reaction: Enantioselective Synthesis of Axially Chiral N-Arylindoles
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An efficient organocatalytic atroposelective three-component cascade reaction of 2,3-diketoesters, aromatic amines, and 1,3-cyclohexanediones has been developed for the highly enantioselective synthesis of axially chiral N-arylindoles. The success of this method derives from the use of a newly developed second-generation chiral spirocyclic phosphoric acid as the catalyst. In addition, this protocol was extended to the synthesis of an axially chiral monophosphorus ligand.
- Wang, Lei,Zhong, Jialing,Lin, Xufeng
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supporting information
p. 15824 - 15828
(2019/10/28)
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- Synthesis and Optical Resolution of 3,3,3′,3′-Tetramethyl-1,1′-spirobiindane-7,7′-diol
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A novel chiral C 2-symmetric spiro diol, 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-7,7′-diol (TMSIOL), was conveniently prepared via practical seven-step route from Bisphenol A in 45.1% overall yield. l-Menthyl chloroformate is used as optical r
- Zhou, Qiaoxia,Pan, Rihuang,Shan, Huanyu,Lin, Xufeng
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p. 557 - 563
(2019/01/10)
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- Diamine monomer, preparation method therefor, polyimide and preparation method therefor
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The invention relates to the technical field of organic chemistry and particularly relates to a diamine monomer, a preparation method therefor, polyimide and a preparation method therefor. According to the diamine monomer provided by the invention, the diamine monomer provided by the invention contains a spiro center (two rings share one atom) and has a non-coplanar structure, the rigidity of molecular chains is improved, and thus, the condition that continuous micropores are formed inside polyimide, holes are many, and the molecular structure is loose is caused due to the fact that macromolecular principal chains in the polyimide prepared from the diamine monomer provided by the invention cannot rotate freely and effective accumulation among the molecular chains is inhibited, so that thegas permeability, solubility and the like of a polyimide film prepared from the diamine monomer provided by the invention can be improved on the premise that selectivity is kept; and furthermore, thepolyimide prepared from the diamine monomer provided by the invention has relatively good solubility and light transmittance.
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Paragraph 0098-0100
(2019/04/10)
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- Diacid monomer and preparing method thereof and polyamide and preparing method thereof
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The invention relates to the technical field of organic chemistry, in particular to a diacid monomer and a preparing method thereof and polyamide and a preparing method thereof. The diacide monomer contains a conch center (two rings share one atom) and is provided with a noncoplanar structure, so that the molecular chain rigidity is improved, the polymer backbone in polyamide prepared from the diacid monomer cannot rotate freely, effective accumulation among molecular chains is hindered, and accordingly continuous microholes are formed in polyamide; a large quantity of empty holes exist, the molecular structure is loose, and thus on the premise that the selectivity of a polyamide thin film prepared from the diacid monomer can be maintained, the permeability, solubility and the like of gasare improved. In addition, the polyamide prepared from the diacid monomer has good solubility.
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Paragraph 0095-0097
(2019/05/04)
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- Phosphine ligand compounds based on tetramethylspirobiindane skeleton, intermediate of compounds, and preparation method and application of compounds
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The invention discloses phosphine ligand compounds based on a tetramethylspirobiindane skeleton, an intermediate of the compounds, and a preparation method and application of the compounds. The phosphine ligand compounds are compounds having a structure r
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Paragraph 0056; 0057; 0058; 0059
(2018/11/03)
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- Sulfonyl-containing polymeric material with rigid and contorted divinyl crosslinker
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Sulfonyl-containing polymeric materials are prepared by treating a precursor polymeric material with a sulfonyl-containing compound. The precursor polymeric materials are formed from a polymerizable composition that contains a crosslinker that is a free-radically polymerizable spirobisindane monomer. The sulfonyl-containing polymeric material can be used as an ion exchange resin.
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Page/Page column 21-22
(2018/04/14)
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- Lowering Molecular Symmetry To Improve the Morphological Properties of the Hole-Transport Layer for Stable Perovskite Solar Cells
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Inspired by the structural feature of the classical hole-transport material (HTM), Spiro-OMeTAD, many analogues based on a highly symmetrical spiro-core were reported for perovskite solar cells (PSCs). However, these HTMs were prone to crystallize because of the high molecular symmetry, forming non-uniform films, unfavorable for the device stability and large-area processing. By lowering the symmetry of spiro-core, we report herein a novel spirobisindane-based HTM, Spiro-I, which could form amorphous films with high uniformity and morphological stability. Compared to the Spiro-OMeTAD-based PSCs, those containing Spiro-I exhibit similar efficiencies for small area but higher ones for large area (1 cm2), and especially much higher air stability (retaining 80 % of initial PCE after 2400 h storage without encapsulation). Moreover, the Spiro-I can be synthesized from a cheap starting material bisphenol A and used with a small amount for the device fabrication.
- Wang, Xuchao,Zhang, Jing,Yu, Shuwen,Yu, Wei,Fu, Ping,Liu, Xuan,Tu, Dandan,Guo, Xin,Li, Can
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supporting information
p. 12529 - 12533
(2018/09/06)
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- Sulfonyl-containing polymers based on free-radically polymerizable spirobisindane monomers
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Sulfonyl-containing polymeric materials and methods of making these materials are provided. More specifically, the sulfonyl-containing polymeric materials are prepared by treating a precursor polymeric material with a sulfonyl-containing compound. The precursor polymeric material is formed from a polymerizable composition that contains a free-radically polymerizable spirobisindane monomer. The sulfonyl-containing polymeric material is porous. The size of the pores can be in the microporous region, mesoporous region, or both depending on the particular monomers and reaction conditions used to form the precursor polymeric material.
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Page/Page column 22; 23
(2018/04/13)
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- Production of spirobiindane (by machine translation)
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PROBLEM TO BE SOLVED: To produce 6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobiindanes from commercial raw material with high selectivity.SOLUTION: In a reaction step to produce a compound represented by (formula 1) from a compound represented by (formula 2) in a reactor, while water is removed in the presence of acetone, the spirobiindane compound represented by (formula 1) is produced, wherein R1-R6 and R7-R12 are independently, H, a hydroxyl group, a halogen atom, an alkyl group with C12 or less, or the like.
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Paragraph 0285; 0286; 0292; 0300; 0312; 0317; 0322; 0330
(2017/12/01)
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- The benzoxazine compounds, its manufacturing method and a benzoxazine resin (by machine translation)
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[A] good heat resistance, the heat is difficult to be decomposed, high glass transition temperature and a method of manufacturing a novel benzoxazine compounds. [Solution] spirobisindane spiro bisque romance backbone or backbone, such as benzoxazine compo
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Paragraph 0060; 0061
(2017/06/15)
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- Benzoxaxine compound, polymer of benzoxaxine compound, preparation method of benzoxaxine compound and polymer and binding agent obtained through benzoxaxine compound and polymer
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The invention relates to a benzoxaxine compound containing spirobiindan, a polymer of the benzoxaxine compound, a preparation method of the benzoxaxine compound and the polymer and a binding agent obtained through the benzoxaxine compound and the polymer.
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Paragraph 0133; 0134; 0135
(2017/06/02)
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- DIAMINE-BASED COMPOUND AND POLYMER PREPARED BY USING THE SAME
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The present invention relates to a diamine-based compound containing a spiro-bisindane structure and a polymer manufactured by using the same as a monomer. In chemical formula 1, R1 and R2 are the same or different and are -O(CH_2)Y respectively wherein the Y is selected from a group consisting of hydrogen, a C1-C50 alkyl group and a C1-C50 alkyl oxy group. In the present invention, provided is a polymer manufactured by using a diamine-based compound as a monomer of chemical formula 1 wherein the diamine-based compound having a spiro-bisindane structure is new compound and denoted by chemical formula 1.
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Paragraph 0040 - 0043
(2016/10/17)
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- Synthesis and gas transport properties of hydroxyl-functionalized polyimides with intrinsic microporosity
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A newly designed diamine monomer, 3,3,3′,3′-tetramethyl-1, 1′-spirobisindane-5,5′-diamino-6,6′-diol, was successfully used to synthesize two types of polyimides for membrane-based gas separation applications. The novel polymers integrate significant microporosity and polar hydroxyl groups, showing the combined features of polymers of intrinsic microporosity (PIMs) and functional polyimides (PIs). They possess high thermal stability, good solubility, and easy processability for membrane fabrication; the resulting membranes exhibit good permeability owing to the intrinsic microporosity introduced by the highly contorted PIM segments as well as high CO2/CH4 selectivity that arises from the hydroxyl groups. The membranes show CO2/CH4 selectivities of >20 when tested with a 1:1 CO2/CH4 mixture for feed pressures up to 50 bar. In addition, the incorporation of hydroxyl groups and microporosity in the polymers enhances their affinity to water, leading to remarkable water sorption capacities of up to 22 wt % at 35 °C and 95% relative humidity.
- Ma, Xiaohua,Swaidan, Raja,Belmabkhout, Youssef,Zhu, Yihan,Litwiller, Eric,Jouiad, Mustapha,Pinnau, Ingo,Han, Yu
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experimental part
p. 3841 - 3849
(2012/08/13)
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- Molecular tectonics: From 1-D interwoven racemic chains to quadruple-stranded helices
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The combination of two positional isomers tectons 1 and 2, based on a racemic 1,1′-spirobi(indane) scaffold bearing two pyridine units, with HgCl2 affords doubly interwoven and quadruple-stranded helical architectures, respectively.
- Lin, Mei-Jin,Jouaiti, Abdelaziz,Kyritsakas, Nathalie,Hosseini, Mir Wais
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scheme or table
p. 115 - 117
(2010/04/01)
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- HIGH REFRACTIVE INDEX MONOMERS, COMPOSITIONS AND USES THEREOF
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The invention relates to novel sulfur-containing (meth)acrylic monomers and compositions thereof characterized by a high refractive index, for optical and industrial applications. The invention also relates to a method for preparing high refractive index polymeric materials and more specifically to a method for formation of ultraviolet cast optical lenses and compositions thereof comprising the sulfur-containing (meth)acrylic monomers.
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Page/Page column 42-43
(2008/12/08)
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- Process for preparing enantiomerically pure 1,1'-spirobiindane-6,6'-diol derivatives
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The present invention relates to a method for the chemical separation of the enantiomers of 1,1′-spirobiindane-6,6′-diol derivatives comprising providing a racemic chiral 1,1′-spirobiindane-6,6′-diol derivative, reacting a nonracemic chiral component with
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Page/Page column 5
(2008/06/13)
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- LIQUID-CRYSTAL COMPOSITIONS COMPRISING CHIRAL COMPOUNDS
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The invention relates to a class of compounds useful as chiral dopants, which compounds are available in both enantiomeric forms, in liquid-crystal formulations. Such formulations are advantageous in displays and various other products.
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Page/Page column 18
(2008/06/13)
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- Generation and synthetic uses of stable 4-[2-isopropylidene]-phenol carbocation from bisphenol A
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(Equation Presented) Stable 4-[2-isopropylidene]-phenol carbocation, IPP cation 1, was generated readily by addition of bisphenol A in concentrated sulfuric acid at ambient temperature, and the cation could be used for facile syntheses of 4-isopropenyl phenol (IPP), IPP dimers, and spiro-bisphenol derivatives.
- Chen, Wei-Fu,Lin, Hsing-Yo,Dai, Shenghong A.
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p. 2341 - 2343
(2007/10/03)
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- A new class of HIV-1 integrase inhibitors: The 3,3,3',3'-tetramethyl- 1,1'-spirobi(indan)-5,5',6,6'-tetrol family
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Integration is a required step in HIV replication, but as yet no inhibitors of the integration step have been developed for clinical use. Many inhibitors have been identified that are active against purified viral- encoded integrase protein; of these, many contain a catechol moiety. Though this substructure contributes potency in inhibitors, it is associated with toxicity and so the utility of catechol-containing inhibitors has been questioned. We have synthesized and tested a systematic series of derivatives of a catechol-containing inhibitor (1) with the goal of identifying catechol isosteres that support inhibition. We find that different patterns of substitution on the aromatic ring suffice for inhibition when Mn2+ is used as a cofactor. Importantly, the efficiency is different when Mg2+, the more likely in vivo cofactor, is used. These data emphasize the importance of assays with Mg2+ and offer new catechol isosteres for use in integrase inhibitors.
- Molteni, Valentina,Rhodes, Denise,Rubins, Kathleen,Hansen, Mark,Bushman, Frederic D.,Siegel, Jay S.
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p. 2031 - 2039
(2007/10/03)
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- Synthesis, crystal structure, magnetic, and electron paramagnetic resonance properties of a spiroconjugated biradical. Evidence for spiroconjugation exchange pathway
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A spiroconjugated nitronyl nitroxide biradical, 6,6'-(4,4,5,5- tetramethylimidazolidine-3-oxide-1-oxyl)-3,3,3',3'-tetramethyl-1,1'- spirobisindane (1), has been prepared by functionalization of a 3,3,3',3'- tetramethyl-1,1'-spirobisindane framework followed by Ullman condensation and subsequent oxidation. The biradical crystallizes in the monoclinic space group C2/c with four molecules in the unit cell of dimensions a = 24.861-(10) A, b = 12.129(3) A, and c = 12.258(6) A. X-ray analysis of a blue-plate single crystal has revealed dihedral angles of 28°between the nitronyl nitroxide moiety and aromatic ring with intramolecular through space radical- radical distances of 8.25 and 10.11 A. In the solid state, the temperature dependence of the molar magnetic susceptibility reveals antiferromagnetic interactions. These interactions are best fit using a pair model, affording the value J = -4.0 cm-1 where J is the interaction parameter appearing in the spin Hamiltonian H = -JS1·S2. The field dependence of the magnetization measured at 2 K is consistent with a pair model. Frozen matrix EPR spectra of biradical 1 in CH2Cl2 at 100 K shows a half field transition at 1700 G. Temperature dependence of the half field transition intensity has been found to be consistent with a ground singlet state and thermally accessible triplet state. The magnetic interaction observed in the solid state is also observed in solution. Thus, room-temperature solution spectra display a nine-line pattern, with hyperfine coupling to four 'equivalent' nitrogen atoms and a hyperfine coupling constant a(N) = 3.8 G. Temperature dependence of the solution EPR spectra of biradical 1 displays alternating line width effects caused by conformational dynamics in solution. This behavior has been attributed to modulation of exchange and hyperfine interactions most likely caused by rotational motion about the nitronyl nitroxide-phenyl bond. Biradical 1 therefore exists as a ground-state singlet with a thermally accessible triplet at ca. 4 cm-1 higher in energy with a conformational dependence of intramolecular exchange in solution. This coupling may present evidence for spiroconjugation as an exchange pathway. Density functional calculations (B3/6-311G(D)) have been performed to investigate this possibility.
- Frank, Natia L.,Clerac, Rodolphe,Sutter, Jean-Pascal,Daro, Nathalie,Kahn, Olivier,Coulon, Claude,Green, Michael T.,Golhen, Stephane,Ouahab, Lahcene
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p. 2053 - 2061
(2007/10/03)
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- Resolution of Binaphthols and Spirobiindanols Using Cholesterol Esterase
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Cholesterol esterase (EC 3.1.1.13) catalyzes the hydrolysis of steroid, binaphthol, and spirobiindanol esters.The hydrolysis of binaphthol and spirobiindanol esters is enantiospecific and can be used to resolve these materials.Simple, synthetic-scale (200 g) procedures are detailed for the resolution of -2,2'-diol (1) and 2,2',3,3'-tetrahydro-3,3,3',3'-tetramethyl-1,1'-spirobi-6,6'-diol (6).Resolution of 1 involved hydrolysis of the dipentanoate ester catalyzed by crude, inexpensive enzyme (bovine pancreas acetone powder) and yielded each enantiomer in > 60percent of theoretical yield with >/= 99percent enantiomeric purity.Similar resolution of 6 by hydrolysis of the dihexanoate ester yielded each enantiomer in > 50percent of theoretical yield with > 95percent enentiomeric purity.These resolution involve two enzymic reactions: hydrolysis of the diester to the monoester followed by hydrolysis of the monoester to the diol.A theoretical analysis of such two-step resolutions suggests that two-step resolutions can yield products with higher enantiomeric purity than can single-step resolutions.
- Kazlauskas, Romas J.
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p. 4953 - 4959
(2007/10/02)
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- Process for producing 6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobiindane
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A novel process for producing 6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobiindane of the formula (1) STR1 which comprises heat-treating 2,2-bis(4-hydroxyphenyl)propane in the presence of a superacid-type resin or a perfluoroalkanesulfonic acid.
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