CN106631986A - Crystal structure for B-type 3,6-diiodo-N-phenylcarbazole and preparation method thereof - Google Patents
Crystal structure for B-type 3,6-diiodo-N-phenylcarbazole and preparation method thereof Download PDFInfo
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- CN106631986A CN106631986A CN201610865572.5A CN201610865572A CN106631986A CN 106631986 A CN106631986 A CN 106631986A CN 201610865572 A CN201610865572 A CN 201610865572A CN 106631986 A CN106631986 A CN 106631986A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- 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
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Abstract
The invention discloses a crystal structure for B-type 3,6-diiodo-N-phenylcarbazole and a preparation method thereof, belonging to the field of photoelectric materials. Concretely, the preparation method is as follows: dissolving 0.1 mmol of 3,6-diiodo-N-phenylcarbazole in 10 mL of an ethyl acetate solvent, carrying out standing for 1 week, and carrying out filtering and washing so as to prepare a bulk colorless crystal of the B-type 3,6-diiodo-N-phenylcarbazole, wherein the melting point of the colorless bulk crystal is 289 to 291 DEG C; and the crystal structure of the colorless bulk crystal belongs to a monoclinic space group of P21/n, and has cell parameters as described in the specification. The compound provided by the invention is an intermediate of an excellent photoelectric material.
Description
Technical field
The invention belongs to photoelectric material, field of fine chemical, relate generally to the crystal knot of a kind of pair of iodo carbazole derivates
Structure is studied.
Background technology
Carbazole has great application in fields such as organic electroluminescent light, electroluminescent and nonlinear optical elements,
Particularly carbazole derivates are widely used as hole transport layer material(Li Meng, Lv Hongfei, Li Shuhui etc. the bromo- 9- benzene of 3-
The synthesis [J] of base carbazole. Heilungkiang science. 2012,3 (1):26-31).Organic molecule and polymerizable compound based on carbazole
Be owned by fabulous cavity transmission ability, film forming property and thermal property, these advantageous properties all contribute to carbazole and its
Derivative is applied in the exploitation of organic electroluminescent device and photovoltaic cell(Yu Tao etc. carbazole derivates are sent out in organic electroluminescence
Progress [J] in luminescent material. New Chemical Materials. 2009,37 (5):6-8).In these carbazole derivates, halo
Carbazole is to synthesize these derivative key intermediates.Therefore, researching and developing halo carbazole becomes organic electroluminescent device
It is inevitable.
It is well known that the difference of crystal formation causes the physical property of crystal more difference occur.The especially double iodine of polymorphic
Research for the crystal structure of carbazole derivates still has no document report.It is contemplated that studying a kind of double iodo carbazoles of Type B
The crystal structure of derivative.
The content of the invention
It is iodo- that the present invention provides a kind of Type B 3,6- bis-NCrystal structure of-phenyl carbazole and preparation method thereof.This pair of iodo
Carbazole derivates are very active due to atomic iodine, and the design of other monomers containing carbazole or polymer is synthesized after being and offer is constructed
More possibility.
The technical problem to be solved is achieved by the following technical programs:A kind of Type B 3,6- bis- is iodo-N- benzene
The preparation method of base carbazole crystal structure is as follows:By 9- phenyl carbazoles (0.2433 g, 0.1 mmol), KI (0.6640
G, 4.0 mmol) and Potassiumiodate (0.4277 g, 2.0 mmol) mix with 50ml glacial acetic acid room temperatures.135 DEG C are heated to, are returned
Stream is after 18 hours.Reactant liquor naturally cools to room temperature.Suction filtration, with the hypo solutions of 50ml 10% and 30ml distillation water washings
Precipitation.Weigh 0.1mmol 3,6- bis- iodo-N- phenyl carbazole is dissolved in the ethyl acetate solvent of 10 mL, stands 1 week, is filtered,
Washing, prepares a kind of Type B 3, and 6- bis- is iodo-NThe colourless bulk crystals of-phenyl carbazole.Its crystal structure belongs to monoclinic system,P21/cSpace group, cell parameter is
。
Beneficial effects of the present invention:The advantage of carbazole compound is combined, this pair of iodo carbazole compound is easy to
Reacted with alkynyl, boronate aromatic is contained, other monomers containing carbazoles are constructed for after or polymer is provided
More possibilities.And the carbazole ring in the compound of gained has the aromatic rings of fluorescence property, for optical material one is provided
May.
Description of the drawings
Fig. 1, Type B 3,6- bis- of the invention are iodo-NThe crystal structure figure of-phenyl carbazole.
Fig. 2, Type B 3,6- bis- of the invention are iodo-NThe one-dimensional chain figure of-phenyl carbazole.
Fig. 3, Type B 3,6- bis- of the invention are iodo-NThe X-Y scheme of-phenyl carbazole.
Fig. 4, Type B 3,6- bis- of the invention are iodo-NThe accumulation graph of-phenyl carbazole.
Specific 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.
Embodiment:Type B 3,6- bis- is iodo-NThe preparation of-phenyl carbazole crystal structure
The 3,6- bis- for weighing 0.1 gram is iodo-N- phenyl carbazole, in being dissolved in 10 milliliters of ethyl acetate, filters, and after standing 1 week, obtains
A kind of Type B 3,6- bis- is iodo-NThe colourless bulk crystals of-phenyl carbazole.Fusing point:289-291oC。
Then it is above-mentioned Type B 3,6- bis- is iodo-N- phenyl carbazole compound carries out structural characterization.
3,6- bis- is iodo- for the Type BN- phenyl carbazole compound uses on computers SHELXTL by mono-crystalline structures diffraction
Program bag completes structure determination and refine.Compound 3,6- bis- is iodo-NThe crystallographic parameter of-phenyl carbazole is shown in Table 1.
Type B 3,6- bis- is iodo- for table 1NThe cell parameter of-phenyl carbazole
。
As shown in Figure 1, single crystal X-ray analysis show that asymmetric cell is only iodo- by independent 3 a, 6- bis-N- phenyl
The molecular composition of carbazole.Crystal structure shows, iodo- in 3,6- bis-NIn the compound of-phenyl carbazole, 3 and 6 points of carbazole
It is not connected to an atomic iodine.Bond distance is respectively 2.113 and 2.085 between carbon atom and atomic iodine.
Fig. 2 is represented along structure cellbThe one-dimensional chain of axle.It is intermolecular to there is C-H π effects between two neighboring compound
Power.The active force is made up of C6-H6 π, and π aromatic rings is made up of C1-C2-C3-C4-C5-C6.This supermolecule
The distance of active force is 3.693, and angle is 137o.Along structure cellbThe direction of axle, these active forces are these adjacent compounds
Connect into one-dimensional chain.
Fig. 3 represents edgeabThe two-dimensional layer in face.Along structure cellabFace, by intermolecular C-H π active forces by multiple phases
Adjacent one-dimensional chain is extended to a two-dimensional layer with 1.3nm thickness.These intermolecular forces have C3-H3A πCg8With
C-H···πCg9, the distance of its active force is respectively 3.694 and 3.707, and its angle is 150o.Here, by carbazole
C13-C14-C15-C16-C17-C18 composition aromatic rings Cg9 in ring, and aromatic rings Cg8 is by C7- C8-C9-C10-C11-
C12 is constituted.In addition to C-H π active forces, it was found that π pi accumulation active forces, such as, Cg8Cg9 it
Between the distance of sedimentation power be that the distance of π pi accumulation active forces between 3.741, Cg9Cg8 is
3.741Å。
Fig. 4 represents the accumulation graph of compound.Above-mentioned two-dimensional nano layer is further piled into a Magnetic Properties of Three-Dimensional Supramolecular Complex structure.
Embodiment described above only expresses embodiments of the present invention, and its description is more concrete and detailed, but can not
Therefore the restriction to the scope of the claims of the present invention is interpreted as, as long as the skill obtained in the form of equivalent or equivalent transformation
Art scheme, all should fall within the scope and spirit of the invention.
Claims (6)
1. a kind of Type B 3,6- bis- is iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that:The crystal structure of described compound
Belong to monoclineP21/ n space groups, its cell parameter is:
,
Its crystal structure figure as scheme I shown in,
Figure I.
2. a kind of Type B 3,6- bis- according to claim 1 is iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that prepare
Process is as follows:0.1mmol 3,6- bis- are iodo-N- phenyl carbazole is dissolved in the ethyl acetate solvent of 10 mL, stands 1 week, is filtered,
Washing, prepares a kind of Type B 3, and 6- bis- is iodo-NThe colourless bulk crystals of-phenyl carbazole.
3. a kind of Type B 3,6- bis- according to claim 1 is iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that it melts
Point range 289-291 degree.
4. a kind of Type B 3,6- bis- according to claim 1 is iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that structure cell
It is only iodo- containing a 3,6- bis- in asymmetric cellN- phenyl carbazole molecule.
5. a kind of Type B 3,6- bis- according to claim 1 is iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that:
It is intermolecular to there is C-H π active forces between two neighboring compound;The active force is made up of C6-H6 π, and π
Aromatic rings is made up of C1-C2-C3-C4-C5-C6;The distance of this supermolecular mechanism power is 3.693, and angle is 137o;Edge
Structure cellbThe direction of axle, these active forces connect into one-dimensional chain these adjacent compounds;Along structure cellabFace, by molecule
Between C-H π active forces multiple adjacent one-dimensional chains are extended into a two-dimensional layer with 1.3nm thickness;Its active force
Distance respectively 3.694 and 3.707, and its angle is 150o;In addition to C-H π active forces, it was found that have
π pi accumulation active forces, such as, the distance of the sedimentation power between Cg8Cg9 is 3.741, Cg9
The distance of the π pi accumulation active forces between Cg8 is 3.741.
6. a kind of Type B 3,6- bis- according to claim 1 is iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that:It is described
Compound be a kind of excellent photoelectric material intermediate.
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Citations (8)
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JP2007284411A (en) * | 2006-04-20 | 2007-11-01 | Bando Chem Ind Ltd | New carbazole derivative and its utilization |
JP2008031068A (en) * | 2006-07-27 | 2008-02-14 | Mitsubishi Chemicals Corp | Organic compound, electric charge-transporting material, electric charge-transporting material composition and orgnic electric field light-emitting element |
CN101323587A (en) * | 2007-06-15 | 2008-12-17 | 富士施乐株式会社 | Novel carbazole compound, and polymer thereof |
EP2100880A1 (en) * | 2006-11-16 | 2009-09-16 | Bando Chemical Industries, Ltd. | Novel carbazole derivative and use thereof |
CN101981086A (en) * | 2008-04-02 | 2011-02-23 | 三菱化学株式会社 | Polymer compound, reticulated polymer compound produced by crosslinking the polymer compound, composition for organic electroluminescent element, organic electroluminescent element, organic EL display, and organic el lighting |
CN102153502A (en) * | 2004-10-19 | 2011-08-17 | 株式会社半导体能源研究所 | Carbazole derivative and light-emitting element and light-emitting apparatus using carbazole derivative |
CN102325751A (en) * | 2009-02-18 | 2012-01-18 | 出光兴产株式会社 | Aromatic amine derivative and organic electroluminescent element |
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2016
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Patent Citations (8)
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CN102153502A (en) * | 2004-10-19 | 2011-08-17 | 株式会社半导体能源研究所 | Carbazole derivative and light-emitting element and light-emitting apparatus using carbazole derivative |
JP2007284411A (en) * | 2006-04-20 | 2007-11-01 | Bando Chem Ind Ltd | New carbazole derivative and its utilization |
JP2008031068A (en) * | 2006-07-27 | 2008-02-14 | Mitsubishi Chemicals Corp | Organic compound, electric charge-transporting material, electric charge-transporting material composition and orgnic electric field light-emitting element |
EP2100880A1 (en) * | 2006-11-16 | 2009-09-16 | Bando Chemical Industries, Ltd. | Novel carbazole derivative and use thereof |
CN101323587A (en) * | 2007-06-15 | 2008-12-17 | 富士施乐株式会社 | Novel carbazole compound, and polymer thereof |
CN101981086A (en) * | 2008-04-02 | 2011-02-23 | 三菱化学株式会社 | Polymer compound, reticulated polymer compound produced by crosslinking the polymer compound, composition for organic electroluminescent element, organic electroluminescent element, organic EL display, and organic el lighting |
CN102325751A (en) * | 2009-02-18 | 2012-01-18 | 出光兴产株式会社 | Aromatic amine derivative and organic electroluminescent element |
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