CN106631987A - Crystal structure of type-A 3,6-diiodo-N-phenylcarbazole and preparation method of crystal structure - Google Patents
Crystal structure of type-A 3,6-diiodo-N-phenylcarbazole and preparation method of crystal structure Download PDFInfo
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- CN106631987A CN106631987A CN201610865573.XA CN201610865573A CN106631987A CN 106631987 A CN106631987 A CN 106631987A CN 201610865573 A CN201610865573 A CN 201610865573A CN 106631987 A CN106631987 A CN 106631987A
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- C—CHEMISTRY; METALLURGY
- 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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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Abstract
The invention discloses a crystal structure of type-A 3,6-diiodo-N-phenylcarbazole and a preparation method of the crystal structure. The preparation method of the crystal structure comprises steps as follows: 0.1 g of 3,6-diiodo-N-phenylcarbazole is weighed and dissolved in 5 ml of chloroform, a mixed solution is filtered, a product is left to stand for 3 days, and a colorless bulk crystal is obtained. The crystal structure of type-A 3,6-diiodo-N-phenylcarbazole belongs to a monoclinic system and a P21 space group, and lattice parameters are shown in the specification. The compound is an excellent photoelectric material intermediate.
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
Over the last couple of decades, the scientists and engineers of fluorescent element are studied in the related carbazole phosphor of synthesis
Material achieves many gratifying achievements with the optimal fluorescence structure aspect of design.Some organic molecules and polymerization chemical combination based on carbazole
Thing is 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 in organic electroluminescence
Progress [J] in luminescent material. New Chemical Materials. 2009,37 (5):6-8).For example, in the exploitation of OLED lamps
Cheng Zhong, scientists are concentrated one's energy, and searching is more to possess good thermal property, the material of highlighter-fastness and excellent cavity transmission ability
Material.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- phenyl carbazoles of 3-
Synthesis [J]. Heilungkiang science. 2012,3 (1):26-31).
As described above, although this kind of carbazole compound has good optical property, its crystal structure research report
Road is fewer.The especially crystal structure research of double iodo carbazole derivates still has no document report.This kind of pair of iodo carbazole
It is to synthesize other more excellent photoelectric material intermediates.It is contemplated that the crystal knot of this pair of iodo carbazole derivates of research
Structure.
The content of the invention
It is iodo- that the present invention provides a kind of 3,6- bis-NCrystal structure of-phenyl carbazole and preparation method thereof.This pair of iodo click
Zole derivatives are very active due to atomic iodine, and the design and constructing that other monomers containing carbazole or polymer are synthesized after being is provided
More possibility.
The technical problem to be solved is achieved by the following technical programs:A kind of A types 3,6- bis- are 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.The 3,6- bis- for weighing 0.1 gram is iodo-N- phenyl carbazole, in being dissolved in 5 milliliters of chloroforms, filters, and after standing 3 days, obtains one kind
Colourless bulk crystals.Its crystal structure belongs to monoclinic system,P21Space 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 carbazole ring has the aromatic rings of fluorescence property in the compound of gained, providing one for optical material can
Energy.
Description of the drawings
Fig. 1, A types 3,6- bis- of the invention are iodo-NThe crystal structure figure of-phenyl carbazole.
Fig. 2, A types 3,6- bis- of the invention are iodo-NThe one-dimensional chain figure of-phenyl carbazole.
Fig. 3, A types 3,6- bis- of the invention are iodo-NThe X-Y scheme of-phenyl carbazole.
Fig. 4, A types 3,6- bis- of the invention are iodo-NThe accumulation graph of-phenyl carbazole.
Fig. 5, A types 3,6- bis- of the invention are iodo-NThe ultraviolet-visible spectrogram of-phenyl carbazole.
Fig. 6, A types 3,6- bis- of the invention are iodo-NThe infrared spectrogram 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 3,6- bis- is iodo-NThe preparation of-phenyl carbazole compound.
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, after flowing back 18 hours.Reactant liquor is certainly
So it is cooled to room temperature.Suction filtration, with the hypo solutions of 50ml 10% and 30ml distillation water washing precipitations.The 3 of 0.1 gram are weighed,
6- bis- is iodo-N- phenyl carbazole, in being dissolved in 5 milliliters of chloroforms, filters, and after standing 3 days, obtains a kind of colourless bulk crystals.
Then it is above-mentioned 3,6- bis- is iodo-N- phenyl carbazole compound carries out structural characterization.
The 3,6- bis- is iodo-N- phenyl carbazole compound uses on computers SHELXTL programs by mono-crystalline structures diffraction
Bag completes structure determination and refine.Compound 3,6- bis- is iodo-NThe crystallographic parameter of-phenyl carbazole is shown in Table 1.
3,6- bis- is iodo- for table 1NThe cell parameter of-phenyl carbazole.
As shown in Figure 1, X-ray diffraction analysis shows, compound 1 is with chiral space groupP21Crystallization.In asymmetric list
In unit, two independent 3,6- bis- are there are iodo-NThe molecule of-phenyl carbazole.Crystal structure shows that first 3,6- bis- is iodo-N-
In phenyl carbazole molecule, 3 and 6 in carbazole respectively connected an atomic iodine, and its bond distance is respectively 2.124(9)With
2.054(10)Å.And it is iodo- in second 3,6- bis-NIn-phenyl carbazole molecule, C-I key lengths are 2.043(9)With 2.120
(9)Å.NDihedral angle between-phenyl group and five-membered ring is 52.6oWith 47.4o.Its mean dihedral angle 50o, this is than first
The dihedral angle of molecule is much higher.
Fig. 2 is represented along structure cellbThe one-dimensional chain of axle.It is intermolecular by π π active forces and C- between two neighboring compound
H π active forces are interconnected to one-dimensional chain.These active forces come between carbazole ring, such as:Cg(1)∙∙∙Cg(3) a 3.847(7)Å; Cg(2)∙∙∙Cg(1) a 3.900(7)Å; Cg(2)∙∙∙Cg(3) a 3.727(6)Å; Cg(3)∙∙∙Cg(1) b
3.848(7)Å; Cg(3)∙∙∙Cg(2) b 3.728(6)Å; Cg(6)∙∙∙Cg(7) c 3.890(6)Å; Cg(6)∙∙∙Cg(8) d
3.877(6) Å; Cg(7)∙∙∙Cg(6) d 3.889(6) Å; Cg(7)∙∙∙Cg(8) d 3.761(6) Å; Cg(8)∙∙∙Cg
(6) a 3.876(6) Å; Cg(8)∙∙∙Cg(7) a 3.761(6) Å.Here the symmetric code that a, b and c is expressed as follows respectively:
x,-1+y,z; x,1+y,z;X, -1+y, z and x, 1+y, z.In addition, aromatic rings Cg (1) is by these atomic buildings N (1)-C
(6)-C(1)-C(7)-C(12);Cg (2) is made up of C (1)-C (2)-C (3)-C (4)-C (5)-C (6);Cg (3) is by C
(7)-C (8)-C (9)-C (10)-C (11)-C (12) atomic building;Aromatic rings Cg (6) is by N (2)-C (24)-C (19)-C
(25)-C (30) atomic building;Aromatic rings Cg (7) is made up of C (19)-C (20)-C (21)-C (22)-C (23)-C (24); Cg
(8) it is by these atomic buildings C (25)-C (26)-C (27)-C (28)-C (29)-C (30).In addition, phenyl aromatic ring
On hydrogen and phenyl aromatic ring there is supermolecular mechanism power, for example:C(15)-H(15)∙∙∙Cg(7) a 153o, 3.661(17)
Å; C(18')-H(18')∙∙∙Cg(4) b 135o, 3.663 (16); C(33)-H(33)∙∙∙Cg(2) c 141o, 3.669
(17)Å; C(35)-H(35)∙∙∙Cg(3) d 152o, 3.693 (15).Herea、bWithcRepresent that symmetric code is respectively:1-x,
1/2+y,1-z;x,1+y,z;1-x, -1/2+y, 1-z and-x, -1/2+y, 1-z.Aromatic rings Cg (2), Cg (3), Cg (4) and Cg
(7) respectively by following atomic building:C(1)-C(2)-C(3)-C(4)-C(5)-C(6); C(7)-C(8)-C(9)-C(10)-C
(11)-C(12); C(13)-C(14)-C(15)-C(16)-C(17)-C(18); C(19)-C(20)-C(21)-C(22)-C
(23)-C(24)。
Fig. 3 represents edgeabThe two-dimensional layer in face.By it is intermolecular will be multiple with C-H π active forces by π π active forces
One-dimensional chain is extended to two-dimensional layer.
Fig. 4 represents the accumulation graph of compound.Above-mentioned two-dimensional layer is piled into a Magnetic Properties of Three-Dimensional Supramolecular Complex structure.
Fig. 5 represents that 3,6- bis- is iodo-NThe ultraviolet-visible spectrogram of-phenyl carbazole.As shown in figure 5, finding in 264-377 nm
There is obvious absworption peak in region.Research finds that the maximum absorption band of compound 1 is located at 359 nm.
Fig. 6 represents that 3,6- bis- is iodo-NThe infrared spectrogram of-phenyl carbazole.From infrared spectrum, in 3134 cm-1Place, can
It is divided into fragrant c h bond(νC-H).C=C stretching vibrations on aromatic rings generally occur in 1400-1625 cm-1In the range of.Five
Peak is located at respectively 1595,1500,1463,1427 and 1400 cm-1, this C=C framework that may be attributed to carbazole ring flexible shakes
It is dynamic.In general, the flexural vibrations of the c h bond on aromatic rings generally fall in 1000-1300 cm-1Region.As we are expected
As, several peaks are located in the range of 1278-1014 cm-1, show the presence of phenyl ring.Bands of a spectrum fall in 1014-630 cm-1Area
Domain, vibrate with the plane deformation of aroma system outside C-H faces so as to represent.In 565 and 563 cm-1The strong peak at place is iodine in aromatic ring
Eigen vibration peak.
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 (5)
1. a kind of A types 3,6- bis- are iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that:The crystal structure of described compound
Belong to monoclineP21Space group, its cell parameter is:
Its crystal structure figure as scheme I shown in,
Figure I.
2. a kind of A types 3,6- bis- according to claim 1 are iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that prepare
Method is as follows:The 3,6- bis- for weighing 0.1 gram is iodo-N- phenyl carbazole, in being dissolved in 5 milliliters of chloroforms, filters, and after standing 3 days, obtains
A kind of colourless bulk crystals.
3. a kind of A types 3,6- bis- according to claim 1 are iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that:Structure cell
Two 3,6- bis- are there are in asymmetric cell iodo-N- phenyl carbazole molecule.
4. a kind of A types 3,6- bis- according to claim 1 are iodo-NThe crystal structure of-phenyl carbazole, it is characterised in that:In phase
It is intermolecular to be interconnected to one-dimensional chain by π π active forces and C-H π active forces between adjacent two compounds;These effects
Power comes between carbazole ring, for example:Cg(1)∙∙∙Cg(3) a 3.847(7)Å; Cg(2)∙∙∙Cg(1) a 3.900(7)Å; Cg
(2)∙∙∙Cg(3) a 3.727(6)Å; Cg(3)∙∙∙Cg(1) b 3.848(7)Å; Cg(3)∙∙∙Cg(2) b 3.728(6)Å; Cg
(6)∙∙∙Cg(7) c 3.890(6)Å; Cg(6)∙∙∙Cg(8) d 3.877(6) Å; Cg(7)∙∙∙Cg(6) d 3.889(6) Å;
Cg(7)∙∙∙Cg(8) d 3.761(6) Å; Cg(8)∙∙∙Cg(6) a 3.876(6) Å; Cg(8)∙∙∙Cg(7) a 3.761(6)
Å;In addition, aromatic rings Cg (1) is by these atomic buildings N (1)-C (6)-C (1)-C (7)-C (12);Cg (2) is by C (1)-C
(2)-C (3)-C (4)-C (5)-C (6) compositions;Cg (3) is by C (7)-C (8)-C (9)-C (10)-C (11)-C (12) atom structure
Into;Aromatic rings Cg (6) is by N (2)-C (24)-C (19)-C (25)-C (30) atomic building;Aromatic rings Cg (7) is by C (19)-C
(20)-C (21)-C (22)-C (23)-C (24) compositions;Cg (8) is by these atomic buildings C (25)-C (26)-C (27)-C
(28)-C(29)-C(30);In addition, phenyl aromatic ring hydrogen has supermolecular mechanism power with phenyl aromatic ring;Than
Such as:C(15)-H(15)∙∙∙Cg(7) a 3.661(17)Å; C(18')-H(18')∙∙∙Cg(4) b 3.663(16)Å; C(33)-H
(33)∙∙∙Cg(2) c 3.669(17)Å; C(35)-H(35)∙∙∙Cg(3) d 3.693(15)Å;Aromatic rings Cg (2), Cg (3),
Cg (4) and Cg (7) are respectively by following atomic building:C(1)-C(2)-C(3)-C(4)-C(5)-C(6); C(7)-C(8)-C(9)-
C(10)-C(11)-C(12); C(13)-C(14)-C(15)-C(16)-C(17)-C(18); C(19)-C(20)-C(21)-C
(22)-C(23)-C(24)。
5. a kind of A types 3,6- bis- according to claim 1 are 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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