CN107868005A - The crystal structure and fluorescence property of a kind of carboxylic acid compound - Google Patents

The crystal structure and fluorescence property of a kind of carboxylic acid compound Download PDF

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Publication number
CN107868005A
CN107868005A CN201610856043.9A CN201610856043A CN107868005A CN 107868005 A CN107868005 A CN 107868005A CN 201610856043 A CN201610856043 A CN 201610856043A CN 107868005 A CN107868005 A CN 107868005A
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China
Prior art keywords
carboxylic acid
acid compound
rga
crystal structure
fluorescence property
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CN201610856043.9A
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Chinese (zh)
Inventor
汪永涛
王翠翠
汤桂梅
陈东
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Qilu University of Technology
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Qilu University of Technology
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Priority to CN201610856043.9A priority Critical patent/CN107868005A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention provides crystal structure and the fluorescence property research of a kind of compound of carboxylic acid.Its molecular formula is:C13H16O5.Described carboxylic acid compound is monoclinic system,P21 /nSpace group.Cell parameter：a=12.848 (3),b=4.5539 (10),c=22.328 (5),a=90.00 °,β=101.703 (5) °,γ=90.00 °,V=1279.2(5)Å3, containing carboxylic acid compound due to carboxyl drawing electron group be present, it is more beneficial for Intramolecular electron transfer.Phenyl ring electronics π-conjugated systems be present simultaneously, be more beneficial for electron absorption transition so as to show abundant electrodes transfer behaviour, stronger photoluminescent property can be launched.Also provide possibility as luminescent material for it simultaneously.

Description

The crystal structure and fluorescence property of a kind of carboxylic acid compound
Technical field
The invention belongs to field of functional materials, it is related to the crystal structure and fluorescence property of a kind of carboxylic acid compound.
Background technology
In recent years, the design for having novel structure and the coordination polymer of property has attracted people greatly emerging with synthesis Interest.Being not only due to these compounds has interesting molecular topology, and because they have potential application.Its In there is one of focus for studying always of metal coordinating polymer of fluorescence property.The fluorescence property of metal coordinating polymer, no It is only relevant with central metallic ions, but also with selecting the molecular structure of organic ligand to have much relations.For being matched somebody with somebody from organic For body, from carboxylic acid compound as part main cause：Carboxyl is a drawing electron group, is advantageous to intramolecular charge and turns Move, and there are phenyl ring electronics π-conjugated systems, be advantageous to pi-electron absorptive transition, show abundant electrodes transfer behaviour, can send out Penetrate stronger photoluminescent property.On the other hand because the dissolubility for being carboxyl ligand is relatively preferable, coordination ability is strong, coordination mode spirit Living, very sensitive to the pH value of solution, coordination mode is easy to regulate and control, under carboxylic acid difference pH values can part or all of deprotonation, Multi-form, different degrees of coordination are produced with metal center, can simultaneously serve as hydrogen bond receptor and donor.These advantages are very big Promoted in degree carboxylic acid compound composition metal coordinating polymer illumination field development (B. Y. Li, F. Yang, G. H. Li, D. Liu, Q. Zhou, Z. Shi, S. H. Feng, Cryst. Growth Des.2011, 11, 1475-1485; A. Y. Robin, K. M. Fromm, Coord. Chem. Rev.2006, 250, 2127-2157.)。
The content of the invention
The present invention provides a kind of crystal structure of carboxylic acid compound (abbreviation RGA).This carboxylic acid compound has due to it Donor atom oxygen atom, so with more rich coordination mode and stronger coordination ability, match somebody with somebody for synthesis metal-complexing later The design of position polymer and construct and provide more possibility.
The technical problems to be solved by the invention are achieved by the following technical programs：One kind has carboxylic acid compound, Its molecular formula is: C13H16O5.Described carboxylic acid compound is monoclinic system,P21 /nSpace group.Cell parameter：a=12.848 (3),b=4.5539 (10),c=22.328 (5),a=90.00 °,β=101.703 (5) °,γ=90.00 °,V =1279.2 (5)Å3。
Beneficial effects of the present invention：The advantages of combining carboxylic acid compound, it has the oxygen atom of supplied for electronic, so having More rich coordination mode and stronger coordination ability, for constructing metal coordinating polymer provides more possibilities later, and There is electron-donating group and electron withdraw group, and the aromatic rings with fluorescence property, for the material that lights in the carboxylic acid compound of gained Material provides a possibility
Brief description of the drawings
Fig. 1, RGA molecular structure.
Fig. 2, RGA one-dimensional chain figure.
Fig. 3, RGA room temperature solid fluorogram.
Embodiment
With reference to embodiment, the present invention will be described in detail, and embodiment is only the preferred embodiment of the present invention, It is not limitation of the invention.
By 0.5 mmol 2- (3- ethyoxyls) -4- carbethoxyl group phenylacetic acids（RGA）A certain amount of water heating is added to boil Cooling separates out white needle-like crystals after boiling.
Then above-mentioned carboxylic acid compound is subjected to structural characterization
The carboxylic acid compound is completed by mono-crystalline structures diffraction and with SHELXTL program bags on PC;Compound R GA crystal Learn parameter and be shown in Table 1.
Fig. 1 is to obtain RGA structures by single crystal diffraction method.Contain in the carbomethoxy phenylacetic acid molecules of 2- (3- ethyoxyls) -4 One phenyl ring, an ethyoxyl is connected on the C1 atoms of phenyl ring, a carbomethoxy is connected in the C7 atoms of phenyl ring, on phenyl ring C3 atoms connect a second carboxyl.
The one-dimensional chain figure of RGA shown in Fig. 2.Every a pair of RGA molecules utilize the oxygen atom in carboxylic acid to form O-H O （2.657 Å）Hydrogen bond.Simultaneously, also there is C-H π in every a pair of RGA molecules(C1–C2–C3–C4–C5–C6)Key（2.930 Å）It is logical O-H O the hydrogen bonds and C-H pi bonds for crossing the above form end to end one-dimensional chain.In fig. 2 exist two kinds of hydrogen bond mode A- D mono- is that mark is(8) and(20)。
Fig. 3 is RGA room temperature solid fluorescence spectra.As shown in Figure 3, when excitation wavelength is 284nm, compound There is maximum emission peak in 345nm opening positions in RGA, and this can belong to part π*Caused by → π or π * → n electron transfer.
Embodiment described above only expresses embodiments of the present invention, and its description is more specific and detailed, but can not Therefore the limitation to the scope of the claims of the present invention is interpreted as, as long as the skill obtained using the form of equivalent substitution or equivalent transformation Art scheme, it all should fall within the scope and spirit of the invention.

Claims (4)

  1. A kind of 1. carboxylic acid compound, it is characterised in that：Chemical molecular formula C13H16O5, its entitled 2- (3- ethyoxyls) -4- ethoxy Carbonyl phenylacetic acid（RGA）, its crystal structure is as shown in Figure 1.
  2. 2. according to the carboxylic acid compound described in claims 1, it is characterised in that：Described carboxylic acid compound is monoclinic system,P21 /nSpace group, cell parameter are：a=12.848 (3),b=4.5539 (10),c=22.328 (5),a=90.00 °,β= 101.703 (5) °,γ=90.00 °,V =1279.2(5)Å3, every a pair of RGA molecules utilize the oxygen atom in carboxylic acid to form O-H ∙O（2.657 Å）C-H π also be present in hydrogen bond, simultaneously, every a pair of RGA molecules(C1–C2–C3–C4–C5–C6)Key（2.930 Å）, O-H O hydrogen bonds and C-H pi bonds more than form end to end one-dimensional chain.
  3. 3. the crystal preparation method of the carboxylic acid compound according to claims 1, it is characterised in that：By a certain amount of 2- (3- ethyoxyls) -4- carbethoxyl group phenylacetic acids（RGA）It is added to cooling after a certain amount of water heating is boiled and separates out white needles crystalline substance Body.
  4. 4. according to the carboxylic acid compound described in claims 1, it is characterised in that：There is fluorescence property containing carboxylic acid compound, can As luminescent material.
CN201610856043.9A 2016-09-28 2016-09-28 The crystal structure and fluorescence property of a kind of carboxylic acid compound Pending CN107868005A (en)

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CN107868005A true CN107868005A (en) 2018-04-03

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1500772A (en) * 2002-11-12 2004-06-02 上海三维制药有限公司 Synthetic method of 4-acetoxy-2-ethoxy ethyl benzoate
WO2004101540A2 (en) * 2003-05-14 2004-11-25 Cilag Ag Method for the production of phenylacetic acid derivatives
CN104628518A (en) * 2015-01-28 2015-05-20 湖北益泰药业有限公司 Method for synthesizing repaglinide key intermediate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1500772A (en) * 2002-11-12 2004-06-02 上海三维制药有限公司 Synthetic method of 4-acetoxy-2-ethoxy ethyl benzoate
WO2004101540A2 (en) * 2003-05-14 2004-11-25 Cilag Ag Method for the production of phenylacetic acid derivatives
CN104628518A (en) * 2015-01-28 2015-05-20 湖北益泰药业有限公司 Method for synthesizing repaglinide key intermediate

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