49 results about "Helicene" patented technology

The invention discloses a preparation method of cholesteric-liquid-crystal laminated film. The preparation method includes the steps of (1) introducing, by mass, 0.5wt%-10.0wt% of chirality helicene-type compound, 0wt%-15.0wt% of chirality compound, 0wt%-20.0wt% of liquid-crystal polymerizable monomer and 0wt%-10.0wt% of photoinitiator into a nematic-phase micro-molecule liquid crystal material serving as the main body with a mass fraction of 65.0wt%-98.0wt%, evenly blending the mixture above to obtain a mixed liquid crystal compound system with a phase temperature range which is N* in width; (2) injecting the mixed liquid crystal compound system into a liquid crystal box or making the mixed liquid crystal compound system into liquid crystal film, wherein the thickness of the liquid box or the liquid crystal film is controlled to remain within 2 microns-300microns; (3) conducting ultraviolet light irradiation on the liquid crystal box or the liquid crystal film within a cholesteric phase temperature range to obtain the liquid crystal laminated film. By adopting the preparation method, the liquid crystal film material with a movable central reflected wave section, a wide reflected wave band and a controllable reflection rate can be obtained.

The invention discloses a bistable liquid crystal device with an optical writing or optical erasing function and a preparation method thereof. The bistable liquid crystal device comprises a liquid crystal box or liquid crystal film with the thickness of 2-200 micrometers, and a photoresponsive cholesteric liquid crystal composite system is poured into the liquid crystal box or the liquid crystal film; the photoresponsive cholesteric liquid crystal composite system is prepared from, by mass, 60.0 wt%-97.0 wt% of main micro-molecular liquid crystal materials, 0.5 wt%-15.0 wt% of chiral helicene compounds and 0.2 wt%-30.0 wt% chiral compounds; the initial pitch of the photoresponsive cholesteric liquid crystal composite system is p0, and the pitch rises to p1 or decreases to p2 under the irradiation of excitation light. Through a simple process, the cholesteric liquid crystal device capable of stably switching between a planar texture state and a focal conic texture state under the condition of remote non-contact illumination radiation is prepared.

The invention provides a thermally activated delayed fluorescence luminescent material constructed based on a nitrogen-containing hetero-helicene mother nucleus and applications of the thermally activated delayed fluorescence luminescent material in electroluminescent devices. The invention has the obvious characteristics that: 1) sulfonyl and carbonyl are very good acceptor units in TADF materials, but no sulfonyl and carbonyl double acceptor units exist in one TADF molecule at the same time; the helicene containing heteroatoms has a relatively large helical curvature; 2) directly construction of an MR-TADF material by utilizing the nitrogen hetero helicene parent nucleus is realized; 3) a TICT-TADF material is constructed by taking the nitrogen hetero helicene parent nucleus as a receptor unit, and hanging a donor unit at the periphery; and 4) the novel TADF (including MR-TADF and TICT-TADF) material can cover emission regions such as blue light, green light, red light-near infraredlight and even single-molecule white light. The nitrogen-containing hetero-helicene parent nucleus has the advantages of novel receptor, different TADF construction modes, wide color gamut and the like.

The invention provides a kind of highly condensed ring [6]helicene compounds (I) based on fluorene and naphthalene and synthetic method thereof, and belongs to the technical field of chemical engineering. The highly condensed ring [6]helicene compounds with photoelectric functions are successfully prepared by taking naphthalene and fluorene derivatives as raw materials and employing a photocatalytic cyclization method. The synthetic method has the advantages of high yield, short time, simple operation and the like, also employs common cheap reagents, helps to reduce preparation cost, and is easy for popularization and application. The highly condensed ring [6]helicene compounds based on fluorene and naphthalene has extremely good solubility in different organic solvents, and are beneficial for purification and film making. Multiple highly condensed ring [6]helicene compounds can be obtained by introducing different substitutes. The highly condensed ring [6]helicene compounds based on fluorene and naphthalene is hopeful to be widely applied to fields such as organic electroluminescence, Organic field effect transistor, organic second-order nonlinear or chiral liquid crystal, biological medicines and the like.

The invention provides a carbazole-based high-condensed ring dinitrogen-aza[7]helicene compound (I) and a synthetic method thereof, belonging to the technical field of chemical industry. A high-condensed ring dinitrogen-aza[7]helicene compound with high solubility is prepared successfully by taking a cheap carbazole derivative with a plurality of active spots as a raw material by a photocatalysis loop closing method. The method has the advantages of high yield, short time, easiness for operating and the like; and moreover, the use of an expensive reagent is avoided, so that the preparation cost is reduced, and popularization and application are easy. The carbazole-based high-condensed ring dinitrogen-aza[7]helicene compound (I) is recrystallized in different solvents, so that an inclusion compound crystal comprising different solvents is obtained. The high-condensed ring dinitrogen-aza[7]helicene compound can be widely applied in the fields of super molecular chemistry, asymmetric catalysis, chiral liquid crystals, organic two-order nonlinearity, organic electroluminescence, biological medicine and the like.

The invention discloses a preparation method of a novel photo-induced deformation liquid crystal polymer film based on helicene molecules. The preparation method comprises the following steps: (1) mixing liquid crystal monomers and helicene molecules according to a mass ratio of (95 / 5) to (99 / 1), wherein the simple function group liquid crystal monomers and the bifunctional liquid crystal monomers are mixed according to a mass ratio of (80 / 15) to (1 / 94), the mass fraction of a free radical photo-initiator is 1.0 percent to 5.0 percent, and a total mass fraction of the photo-initiator, the liquid crystal monomers and the helicene molecules is 100 percent; uniformly mixing to obtain a mixed liquid crystal composite system with a wide nematic phase temperature range; (2) pouring the mixedliquid crystal composite system into a liquid crystal box to prepare a liquid crystal film, and controlling the thickness of the liquid crystal film to be 2 micrometers to 50 micrometers; and (3) polymerizing the mixed liquid crystal system in a nematic phase temperature range by virtue of visible light to obtain a film. The liquid crystal polymer film prepared by the invention presents unique curling movement by virtue of the excitation of ultraviolet rays, and has rapid response characteristic.

The invention relates to a fluorescent probe for detecting aluminum ions and zinc ions, which is a helicene derivative. The fluorescent probe has no fluorescence itself, and is complexed with aluminumions or zinc ions, and then the corresponding fluorescence emission peak appears, so that the aluminum ions or zinc ions can be detected by utilizing fluorescence spectroscopy. The preparation methodcomprises the following steps: firstly, reacting methyl salicylate with hydrazine hydrate to form salicylhydrazide, and under the catalysis of piperidine, reacting the salicylhydrazide with an aldehyde group-containing heptadiene compound to generate a fluorescent probe compound I. The fluorescent probe I prepared by the invention has the advantages of simple and convenient synthesis, high yieldand easy preparation, and is suitable for enlargement synthesis and actual production applications. The fluorescent probe can detect the aluminum ions and the zinc ions by using a fluorescence method,and can be applied to the field of ion detection as a new probe. The probe has good molecule selectivity and high sensitivity, has the advantages of fast response and obvious advantages, and has a broad application prospect.

The invention discloses a [5] helicene analog and a [7] helicene analog. The analogs enrich the kind of helicene analogs. The invention also provides a preparation method of the helicene analogs. According to the method, heterocyclic helicene analogs are prepared from a bisimine compound and solid phosgene under the action of a low-valent titanium reagent. The heterocyclic helicene analogs are prepared through utilizing the reduction coupling effect of the low-valent titanium reagent and using the bisimine compound and the solid phosgene as raw materials in the invention. The method has the advantages of easily available raw materials, simplicity, short synthetic route and the like. Additionally, the regulation of the number of rings of the prepared helicene analogs can be realized through controlling the number of aromatic rings in the raw materials in the invention.

The invention provides a helicene derivative, axially chiral amino acid, amine or amino alcohol derivative, and azaperylene, such as compounds represented by Formulae (I), (I′), (II), (II′), and (III):and a method for producing the same.

The invention provides a diaza [6] helicene compound based on carbazole and quinoline and a synthetic method and application of the diaza [6] helicene compound. The diaza [6] helicene compound with a photoelectric function is prepared by taking the carbazole and the quinoline as raw materials and adopting a photocatalytic closed-loop method. The synthetic method provided by the invention has simple synthetic means and is easy to apply, and the preparation cost is reduced since a common low-cost reagent is used. The diaza [6] helicene (I) based on the carbazole and the quinoline has very good solubility in different organic solvents, is favorable to the purification and membrane preparation of the compound and can be used for obtaining multiple aromatic fused-heterocyclic compounds by being introduced into different substituent groups. The invention also provides the application of the diaza [6] helicene compound as a luminescent material in an organic light-emitting diode. The diaza [6] helicene (I) based on the carbazole and the quinoline can be applied to the fields of organic field effect tubes, organic electroluminescence, organic second-order nonlinearity, photovoltaic materials, fluorescent probes, laser dyes and the like.

The invention discloses helicene diphenol hydride, a method for preparing the same and application of the helicene diphenol. A structural formula of the helicene diphenol hydride is shown as a formula I, wherein an R represents hydrogen atoms or bromine atoms, and an R' represents hydrogen atoms or bromine atoms. The helicene diphenol hydride, the method for preparing the helicene diphenol hydride and the application have the advantages that raw materials are low in cost and easy to synthesize, the helicene diphenol hydride is high in product yield, easy to derive and good in stability, and methods for preparing gram-grade quantities of optically pure helicene molecules with excellent heat stability can be implemented.

A quinoxaline-fused dibenzosuberane based helicene has a structure of general formula (1), wherein A is with a structure of general formula (2), general formula (3a) or general formula (3b); X is an oxygen atom, sulfur atom, amino group, or -(CH2)n, wherein n is 0, 1, or 2; R1 and R2 are independently selected from the group consisting of a hydrogen atom, a halogen atom, general formula (4), general formula (5) and general formula (6); and R3 to R15 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group, an alkenyl group, an aryl group, and an amino group.

The invention relates to a benzo[5]helicene-based conjugated polymer as well as a preparation method and application thereof. The polymer has a structure as shown in a formula I, wherein R is independently selected from substituted or unsubstituted linear or branched alkyl having a carbon number of 1-20; Ar is independently selected from -aryl-, -heteroaryl-, -acetenyl-aryl-acetenyl- and -acetenyl-heteroaryl-acetenyl-, and the aryl and heteroaryl can be randomly substituted by a substituent group; n is the number of repetitive units of the polymer, and is more than or equal to 3. The polymer can be used for detecting nitro aromatic explosives, and optimally used for detecting the nitro aromatic explosives in a liquid phase or a gaseous phase.

The invention discloses a chiral helicene with a binaphthol structure, and further provides a preparation method of the chiral helicene. According to the method, chiral binaphthol aldehyde is used asa raw material, and the chiral helicene is synthesized by alkene and photocatalysis ring closure. The chiral helicene with the binaphthol structure has the advantages that the raw material is easily obtained, a synthesizing method is simple, a synthesizing route is short and the like. The obtained chiral helicene compound can be applied to the field of asymmetric catalysis or chiral recognition.

The invention relates to an asymmetric thiophene [7] helicene isomer as well as a preparation method and application thereof. The preparation method comprises the following steps: preparing an asymmetric dithienothiophene dimer compound through a coupling reaction, carrying out LDA deprotonation on the asymmetric dithienothiophene dimer compound, and carrying out (PhSO2)2S thiocyclization to prepare the double-TMS substituted asymmetric thiophene [7] helicene isomer. The brand-new asymmetric thiophene [7] helicene isomer has an excellent performance, is particularly suitable for being used asan organic semiconductor material, and is applied to organic light emitting diodes, organic field effect transistors and organic solar cells.

The invention provides a chrysene-based aza [7] helicene compound as well as a preparation method and application thereof. The chrysene-based aza [7] helicene compound can be used as a hole transport material, and the hole migration rate of the chrysene-based aza [7] helicene compound is high. Experimental results show that the energy conversion efficiency of a perovskite solar cell device prepared by using the prepared chrysene-based aza [7] helicene compound as a hole transport layer can reach as high as 17.1% to 19.5%.

The invention relates to a probe for detecting copper ions and zinc ions. The probe is an imine derivative of [5] helicene. The imine derivative is complexed with copper ions, so that obvious absorption peaks appear in a visible light area, and the copper ions can be detected by using an ultraviolet-visible spectrum. The imine derivative is complexed with zinc ions, so that fluorescence is raised, and the zinc ions can be detected by using a fluorescence spectrum. A preparation method comprises the following steps: firstly, performing a reaction on a [5] helicene compound with hydroxyl and chloromethyl methyl ether; performing a reaction with butyl lithium and DMF continuously to introduce a formyl group on a ortho-position of hydroxyl; and performing a reaction with an amino compound continuously to generate the [5] helicene imine derivative DC. The probe provided by the invention has the advantages that the prepared helicene derivative DC is simple and convenient to synthesize, high in yield, easy to prepare and suitable for amplified synthesis and actual production and application; bivalent copper ions can be detected by using the ultraviolet-visible spectrum, and the bivalent zinc ions can be detected by means of the fluorescence method; the probe as a novel probe can be applied to the field of ion detection; the probe is good in molecular selectivity and high in sensitivity, has the advantages of fast response and obvious phenomenon, and has a wide application prospect.

The invention discloses an organic electroluminescent material containing a helicene structure, and an electroluminescent device. The organic electroluminescent material is a novel compound containinga helicene structure, and can be used as a host material in an electroluminescent device. The novel compounds can provide high current efficiency and high external quantum efficiency, and provide good device performance.

The invention discloses a chiral azaspirene salt compound and a preparation method thereof. The invention provides a preparation method of a compound 1. The preparation method comprises the followingsteps: in a solvent, in the presence of a rhodium catalyst, an oxidant and a chiral acid, reacting a compound as shown in a formula II with a compound as shown in a formula III to obtain the compound1, wherein the compound 1 is a chiral azaspirene salt compound as shown in a formula I or a chiral azaspirene salt compound as shown in a formula I. The method can be used for synthesizing the chiralazaspirene salt compound in one step, has excellent yield and enantioselectivity, and is relatively good in substrate universality.

The invention relates to diseleno [2,3-b:3',2'-d]thiophene and a preparation method thereof, belonging to the technical field of heterocyclic compounds. The diseleno[2,3-b:3',2'-d]thiophene disclosed by the invention has a structure shown as a formula (1). The diseleno [2,3-b:3',2'-d]thiophene disclosed by the invention is a building module of a novel organic functional material and seleno hetero thiophene helicene, and lays a foundation for development of an organic semiconductor material having excellent semiconductor properties and building of seleno hetero thiophene helicene.

The present disclosure is directed to a traceless directing group in a radical cascade. The chemo- and regioselectivity of the initial attack in skipped oligoalkynes is controlled by a propargyl alkoxy moiety. Radical translocations lead to the boomerang return of radical center to the site of initial attack where it assists to the elimination of the directing functionality via β-scission in the last step of the cascade. In some aspects, the reaction of the present invention is catalyzed by a stannane moiety, which allows further via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of skipped oligoalkynes into polycyclic ribbons of tunable dimensions.

The invention discloses a helicene derivative, a preparation method and application thereof. The structural formula of the helicene derivative is shown in formula I-1 or formula I-2, wherein Ar is phenyl or substituted phenyl; R is an alkane with 1 to 5 carbon atoms or an alkane with 6 carbon atoms ~12 aromatics. The chiral helicene derivatives provided by the invention can be used to prepare chiral organic light-emitting materials, and the organic light-emitting materials have circularly polarized light-emitting properties. The method for preparing chiral helicene derivatives with circularly polarized luminescent properties provided by the present invention has cheap raw materials, simple synthesis method and high product yield; the helicene derivatives provided by the present invention have high racemization energy barrier and good stability And other characteristics, it has a good application prospect in the field of chiral optoelectronic materials.

The invention relates to a probe for detecting copper ions and zinc ions. The probe is an imine derivative of [5] helicene. The imine derivative is complexed with copper ions, so that obvious absorption peaks appear in a visible light area, and the copper ions can be detected by using an ultraviolet-visible spectrum. The imine derivative is complexed with zinc ions, so that fluorescence is raised, and the zinc ions can be detected by using a fluorescence spectrum. A preparation method comprises the following steps: firstly, performing a reaction on a [5] helicene compound with hydroxyl and chloromethyl methyl ether; performing a reaction with butyl lithium and DMF continuously to introduce a formyl group on a ortho-position of hydroxyl; and performing a reaction with an amino compound continuously to generate the [5] helicene imine derivative DC. The probe provided by the invention has the advantages that the prepared helicene derivative DC is simple and convenient to synthesize, high in yield, easy to prepare and suitable for amplified synthesis and actual production and application; bivalent copper ions can be detected by using the ultraviolet-visible spectrum, and the bivalent zinc ions can be detected by means of the fluorescence method; the probe as a novel probe can be applied to the field of ion detection; the probe is good in molecular selectivity and high in sensitivity, has the advantages of fast response and obvious phenomenon, and has a wide application prospect.

The invention belongs to the field of organic magnetic materials, and specifically discloses a quadruple helicene free radical molecule characterized by thermally induced magnetic hysteresis loops of conjugated free radicals. The invention also discloses the preparation method of the quadruple helicene free radical, the thermally induced magnetic switching mechanism and the characteristics of the magnetic switching material. The invention constructs helicene multi-radical molecules, and the temperature can regulate the electronic structure of the free radical molecules and the magnetic exchange effect of spin electrons at the molecular level, so that it can show the change of material magnetism under macroscopic conditions. It can be applied to organic magnetic function conversion materials and organic spintronic devices.

The invention belongs to the field of organic light-emitting materials, and relates to a [7] helicene organic light-emitting material based on triaryl borane and application of the [7] helicene organic light-emitting material in sign reversal of induced circular polarization light emission. Two triaryl borane-based [7] helical alkenes are disclosed which contain one meryl boron or 2-(meryl boron) phenyl substituent in the 9-position of the [7] helical backbone. The substituent group is changed from the rice boron to the 2-(rice boron) phenyl group, so that the GLUM is increased by two times. Circularly polarized light emission and sign reversal.

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a preparation method of a dioxa [5] helicene compound and an application thereof, and the dioxa[5]helicene compound provided by the invention has good potential application prospects in the fields of photoelectric functional materials, asymmetric synthesis application, metal catalysis and the like. The raw materials adopted in the preparation method are cheap, easy to obtain and diversified, the high-yield dioxa [5] pentahelicene compound can be obtained through reaction under the action of alkali which is easy to obtain commercially, operation is easy, reaction conditions are mild, existence of different functional groups can be compatible, the substrate application range is wide, the product yield is high, and the defect that expensive and unavailable raw materials are used in a traditional transition metal catalytic synthesis method is overcome.

The invention provides a naphthalene-based high condensed ring-aza [6] helicene compound (I) and a synthesis method thereof, and belongs to the technical field of chemical engineering. The naphthalene-based high condensed ring-aza [6] helicene compound with a photoelectricity function is successfully prepared from naphthalene and a carbazole derivative serving as raw materials by adopting a photocatalysis ring-closing method. The naphthalene-based high condensed ring-aza [6] helicene compound has the advantages of high yield, short time, simple operation and the like. A common low-cost reagent is used, so that the preparation cost is reduced, and the naphthalene-based high condensed ring-aza [6] helicene compound is easy to popularize and apply. The naphthalene-based high condensed ring-aza [6] helicene compound (I) has very good solubility in different organic solvents, so that the purification of the compound and the preparation of a membrane by using the compound are facilitated. Multiple high condensed ring-aza [6] helicene compounds can be obtained by inserting different substituent groups. The naphthalene-based high condensed ring-aza [6] helicene compound (I) is expected to be widely applied in the fields such as organic electroluminescence, organic field-effect transistors, organic second-order nonlinear or chiral liquid crystal, biological medicines and the like.

The invention discloses an axially chiral solid fluorescent material with a helicene structure, and belongs to the technical field of fluorescent materials. The axially chiral solid-state fluorescent compound provided by the invention has the characteristics of an axially chiral structure and a helicene structure. The solid-state fluorescent compound can emit bright blue fluorescence in an organic solvent and in a solid state, and has relatively high fluorescence quantum yield. The enantiomer of the fluorescent compound has obvious circular dichroism, and can show a circularly polarized luminescence property after being excited. The axial chiral fluorescent material disclosed by the invention has excellent solid-state fluorescence luminous efficiency and chiral optical performance, and has potential application value in the photoelectric field.

The invention relates to an axial chiral azaspirene derivative, a circular polarization luminescent material and a preparation method. The structural formula of a racemate of the axial chiral azahelicene is shown as formula A, the structural formula of a P-type isomer is shown as formula I, the structural formula of an M-type isomer is shown as formula II, a compound shown as formula A or a P-typeisomer shown as formula I or an M-type isomer shown as formula II is taken as a reactant for normal temperature stirring reaction with excessive methyl iodide for 24 hours at under the condition of no additional other solvent, so that the product axial chiral azaspirene derivative can be obtained. The compound is compounded with DNA to form a DNA-helicene compound which can be used as a circularpolarization luminescent material. Compared with the prior art, the method has the advantages of simple synthesis method, high synthesis yield and the like.

The invention discloses a bistable liquid crystal device with an optical writing or optical erasing function and a preparation method thereof. The bistable liquid crystal device comprises a liquid crystal box or liquid crystal film with the thickness of 2-200 micrometers, and a photoresponsive cholesteric liquid crystal composite system is poured into the liquid crystal box or the liquid crystal film; the photoresponsive cholesteric liquid crystal composite system is prepared from, by mass, 60.0 wt%-97.0 wt% of main micro-molecular liquid crystal materials, 0.5 wt%-15.0 wt% of chiral helicene compounds and 0.2 wt%-30.0 wt% chiral compounds; the initial pitch of the photoresponsive cholesteric liquid crystal composite system is p0, and the pitch rises to p1 or decreases to p2 under the irradiation of excitation light. Through a simple process, the cholesteric liquid crystal device capable of stably switching between a planar texture state and a focal conic texture state under the condition of remote non-contact illumination radiation is prepared.