CN110143976A - Based on branching porphyrin-imidodicarbonic diamide small molecule receptor synthetic method and application - Google Patents
Based on branching porphyrin-imidodicarbonic diamide small molecule receptor synthetic method and application Download PDFInfo
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Abstract
The invention belongs to photovoltaic material technical fields, it discloses a kind of based on branching porphyrin-imidodicarbonic diamide small molecule receptor synthetic method and application, porphyrin-imidodicarbonic diamide organic molecule solar cell acceptor material has the structure of formula I, and wherein π is benzene, triphenylamine, the N- phenyl-carbazole for being connected to multiple imidodicarbonic diamide, Tetrabenzene methane or four phenylsilane π bridges.Branching porphyrin of the invention-imidodicarbonic diamide small organic molecule photovoltaic acceptor material improves the light capture ability of material, and has the complementary and level-density parameter of good absorption after combining with narrow band gap polymer donor material PTB7-Th etc.；Such small molecule receptor is applied to organic solar batteries by the present invention, the open-circuit voltage of up to 0.84V can be obtained, 7.7% photoelectric conversion efficiency sufficiently presents the corproporphyrin-imidodicarbonic diamide small molecule receptor and has broad application prospects in organic photovoltaic field.
Description
Technical field
The invention belongs to photovoltaic material technical fields, more particularly to one kind to be based on branching porphyrin-imidodicarbonic diamide small molecule
The synthetic method and application of receptor.
Background technique
With the development of the high speed of society, energy demand exponentially of the people for production and living rises, and traditional energy is such as
The consumption such as coal, petroleum, natural gas is huge, increasingly depleted.At the same time, with the use of chemical energy source, environmental problem is also increasingly
Seriously.Solar energy as feel on the earth part energy formed source, have it is renewable, total amount is huge, it is widely distributed, without dirt
The features such as dye, be always be widely noticed, most active research field.
For industrial civilization based on electricity, solar energy can be directly changed into electric energy by solar battery, be always the weight of research
Point.Compared to other solar batteries, there is organic solar batteries raw material easily to obtain, and synthesis cost is cheap, preparation process
Simply, function can modulate according to demand, and preparation process is simple, can large area preparation, many advantages, such as can be made into flexible device,
It holds out broad prospects in practical application.In current research, that there are absorbing abilities is poor because of fullerene, is difficult to modify, stability
The problems such as poor, at high cost, thus the direction studied is transferred in the exploitation of non-fullerene small molecule receptor material.
Porphyrin and imidodicarbonic diamide are common extinction units, have big conjugated system and high Molar Extinction system
Number, high charge mobility are easy to be modified by common chemical method to change its physicochemical properties.Porphyrin and
The spectral absorption of imidodicarbonic diamide is not overlapped, however porphyrin has strong electron property, is usually applied as donor monomer；
Imidodicarbonic diamide has strong electron withdrawing properties, but its aggregation tendency in solid phase is extremely strong, is unfavorable for point of exciton in the application
From.
Problem of the existing technology is:
Existing photovoltaic acceptor material is low to the absorptivity of light, does not improve the pattern of imidodicarbonic diamide film forming, causes making
The device performances such as standby organic photovoltaic solar battery are poor.And prior art preparation is at high cost, and preparation process is cumbersome.
Solve the meaning of above-mentioned technical problem:
For the present invention using porphyrin as interval base, triphenylamine is bridge, is separately connected 4 PDI units.Triphenylamine itself is four sides
Body configuration, after introducing interval base, reversing the trend between PDI unit is more strong, can further decrease the aggregation of molecule in this way
Trend.
Invention introduces having the porphyrin unit absorbed strongly as interval base in visible region, this makes molecule in 400-
There is excellent absorption in the range of 700nm, enhance photogenerated current.
It is bridge that the present invention, which selects triphenylamine, and preparation cost is cheap, sufficient raw, and preparation process is simple.Simultaneously with it is normal
Business donor PTB7-Th be prepared into achieve after bulk heterojunction solar cell up to 7.65% photoelectric conversion efficiency,
With good application performance and wide application prospect.
Summary of the invention
In order to overcome the disadvantages mentioned above and deficiency of the prior art, the present invention provides one kind to be based on-two acyl of branching porphyrin
The synthetic method and application of imines small molecule receptor.It is multiple to reduce exciton for the excessive aggregation for effectively inhibiting imidodicarbonic diamide
The trend of conjunction, and widened the absorption spectrum of material；Simultaneously by changing porphyrin meso group, the conformation of molecule is had adjusted
And HOMO and lumo energy, to produce important influence to device topography and parameter.
It is a further object of the present invention to provide the preparation methods of above-mentioned porphyrin small organic molecule photovoltaic acceptor material.
Another object of the present invention is to provide the application of above-mentioned porphyrin small organic molecule photovoltaic acceptor material.The porphyrin has
Machine small molecule photovoltaic acceptor material is used to prepare solar battery.
The purpose of the present invention is achieved through the following technical solutions: a kind of porphyrin-imidodicarbonic diamide small organic molecule solar energy
Battery acceptor material, the porphyrin-imidodicarbonic diamide organic molecule solar cell acceptor material have the π in multi-connection site
The non-fullerene organic solar batteries acceptor material of the branching of bridge, general structure such as formula I:
Wherein: π is benzene, triphenylamine, the N- phenyl-carbazole, Tetrabenzene methane or four benzene silicon for being connected to multiple imidodicarbonic diamide
Alkane π bridge；A is imidodicarbonic diamide；M is hydrogen or metal ion；Ar is hydrogen, alkyl, alkoxy, unsubstituted or substituted aromatic radical
Group.
Further, the π be benzene, triphenylamine, the N- phenyl-carbazole for being connected to multiple imidodicarbonic diamide, Tetrabenzene methane or
Four phenylsilane π bridges are one of 1~structural formula of structural formula 5:
Further, the Ar is hydrogen, alkyl, alkoxy, one or more of unsubstituted or substituted aromatic heterocycle, for knot
One of 6~structural formula of structure formula 9:
Wherein, R1With R2It is identical or different, for be 0-20 containing carbon number alkyl, alkoxy, it is for hydrogen that carbon, which is 0,.
One of further, the A is structural formula 11)~structural formula 14):
Further, when the M is metal ion, metal ion is zinc ion, iron ion, nickel ion, magnesium ion, copper ion
Or iridium ion.
Another object of the present invention is to provide a kind of porphyrin-imidodicarbonic diamide organic molecule solar cell receptor materials
The preparation method of material the following steps are included:
It is prepared using [2+2] synthetic method: under atmosphere of inert gases, using organic solvent as reaction medium, passing through catalytic body
System reacts even pyrroles with aldehyde, and subsequent processing obtains porphyrin-imidodicarbonic diamide organic molecule solar cell receptor
Material.
Further, even the structural formula of pyrroles is formula II:
Formula II:
The structural formula of the aldehyde is formula III:
III: A- π-CHO of formula.
Wherein: the even Ar in the structure in pyrroles and the Ar phase in porphyrin small organic molecule photovoltaic acceptor material structural formula I
Together；π in structure and A in aldehyde in porphyrin small organic molecule photovoltaic acceptor material structural formula I π and A it is identical.
Further, the organic solvent is dichloromethane or chloroform, and the catalyst system is trifluoroacetic acid.
The time of reaction is 8 hours.
The aldehyde is identical as the even mole of pyrroles, and the mole of trifluoroacetic acid is to connect pyrroles mole in the catalyst system
The 10% of amount.
Further, the subsequent processing is that reaction solution is cooling, is washed, and extraction is spin-dried for, and then passes through chromatography,
Subsequent to carry out metal coordination again, chromatographic column is pure, is spin-dried for, vacuum drying.
The extraction refers to that methylene chloride is extracted.
Porphyrin-imidodicarbonic diamide small organic molecule described in claim is utilized another object of the present invention is to provide a kind of
The full stress-strain solar battery of solar battery acceptor material preparation.
Compared with prior art, the present invention has the following advantages and beneficial effects:
The present invention connects porphyrin and four imidodicarbonic diamide by π bridging, can effectively widen molecule in the absorption of 400-700nm
Spectrum increases the utilization efficiency to solar energy to improve photogenerated current.
The introducing of interval base and π bridge increases the torsion between imidodicarbonic diamide, effectively inhibits the mistake of imidodicarbonic diamide
Degree aggregation, considerably reduces exciton combined efficiency.
The space structure that the present invention is rolled into a ball by adjusting porphyrin meso bit substituent, can effectively control the space structure of molecule
As to obtain the efficient receptor material with best torsion angle.
The present invention by adjust porphyrin meso bit substituent group electronics give ability, adjust synthetic material HOMO,
Lumo energy, final short circuit current, the open-circuit voltage for influencing device.
Porphyrin small organic molecule photovoltaic acceptor material of the invention by introducing different metal ions in porphyrin cavity,
Adjust extinction coefficient, HOMO, the lumo energy of synthetic material, the final comprehensive performance for influencing device.
Porphyrin small organic molecule photovoltaic acceptor material of the invention has high absorbing properties in visible region, can be with spin coating
Film forming, obtains higher transfer efficiency using organic solar batteries prepared by the material.
Detailed description of the invention
Fig. 1 is under the chloroform and filminess of porphyrin small organic molecule photovoltaic acceptor material prepared by embodiment 2
Uv-visible absorption spectra.
Fig. 2 is that porphyrin small organic molecule photovoltaic acceptor material prepared by embodiment 2 is used to prepare photovoltaic cell, photovoltaic cell
In AM 1.5,100mW/cm-2Current -voltage curve figure under illumination；
Fig. 3 is that porphyrin small organic molecule photovoltaic acceptor material prepared by embodiment 2 is used to prepare photovoltaic cell, photovoltaic cell
In AM 1.5,100mW/cm-2External quantum efficiency curve graph under illumination.
Specific embodiment
Below with reference to embodiment and attached drawing, the present invention is described in further detail, but embodiments of the present invention are not
It is limited to this.
Existing photovoltaic acceptor material is low to the absorptivity of light, does not improve the pattern of imidodicarbonic diamide film forming, causes making
The device performances such as standby organic photovoltaic solar battery are poor.And prior art preparation is at high cost, and preparation process is cumbersome.
In view of the problems of the existing technology, the present invention provides one kind to be based on branching porphyrin-imidodicarbonic diamide small molecule
The synthetic method and application of receptor are explained in detail the present invention below with reference to concrete scheme.
Porphyrin provided in an embodiment of the present invention-imidodicarbonic diamide organic molecule solar cell acceptor material has more
The non-fullerene organic solar batteries acceptor material of the branching of the π bridge of connection site, general structure such as formula I:
Wherein: π is benzene, triphenylamine, the N- phenyl-carbazole, Tetrabenzene methane or four benzene silicon for being connected to multiple imidodicarbonic diamide
Alkane π bridge；A is imidodicarbonic diamide；M is hydrogen or metal ion；Ar is hydrogen, alkyl, alkoxy, unsubstituted or substituted aromatic radical
Group.
In embodiments of the present invention, the π be benzene, triphenylamine, the N- phenyl-carbazole for being connected to multiple imidodicarbonic diamide,
Tetrabenzene methane or four phenylsilane π bridges are one of 1~structural formula of structural formula 5:
In embodiments of the present invention, the Ar is hydrogen, alkyl, alkoxy, one in unsubstituted or substituted aromatic heterocycle
Kind or more, it is one of 6~structural formula of structural formula 9:
Wherein, R1With R2It is identical or different, for be 0-20 containing carbon number alkyl, alkoxy, it is for hydrogen that carbon, which is 0,.
One of in embodiments of the present invention, the A is structural formula 11)~structural formula 14):
In embodiments of the present invention, when the M is metal ion, metal ion is zinc ion, iron ion, nickel ion, magnesium
Ion, copper ion or iridium ion.
The present invention provides a kind of preparation method packet of porphyrin-imidodicarbonic diamide organic molecule solar cell acceptor material
Include following steps:
It is prepared using [2+2] synthetic method: under atmosphere of inert gases, using organic solvent as reaction medium, passing through catalytic body
System reacts even pyrroles with aldehyde, and subsequent processing obtains porphyrin-imidodicarbonic diamide organic molecule solar cell receptor
Material.
In embodiments of the present invention, even the structural formula of pyrroles is formula II:
Formula II:
The structural formula of the aldehyde is formula III:
III: A- π-CHO of formula；
Wherein: the even Ar in the structure in pyrroles and the Ar phase in porphyrin small organic molecule photovoltaic acceptor material structural formula I
Together；π in structure and A in aldehyde in porphyrin small organic molecule photovoltaic acceptor material structural formula I π and A it is identical.
In embodiments of the present invention, the organic solvent is dichloromethane or chloroform, and the catalyst system is trifluoro
Acetic acid.
The time of reaction is 8 hours.
The aldehyde is identical as the even mole of pyrroles, and the mole of trifluoroacetic acid is to connect pyrroles mole in the catalyst system
The 10% of amount.
In embodiments of the present invention, the subsequent processing is that reaction solution is cooling, is washed, and extraction is spin-dried for, then passes through color
Column purification is composed, subsequent to carry out metal coordination again, chromatographic column is pure, is spin-dried for, and is dried in vacuo.
The extraction refers to that methylene chloride is extracted.
The invention will be further described combined with specific embodiments below.
Embodiment 1
The synthesis of compound C provided in an embodiment of the present invention, reaction equation are as follows:
Compound B (514mg, 0.29mmol) is added in 100mL two mouth flask, compound A (77mg, 0.35mmol),
37.5mL methylene chloride is bubbled 20 minutes under the conditions of argon gas, trifluoroacetic acid (3.31mg, 0.029mmol) then is added, normal
It is protected from light and is stirred overnight under temperature.Chloro- 5, the 6- dicyanobenzenes a kind of jade (77mg, 0.339mmol) of 2,3- bis- is then added to stir 1 hour,
Purify in the chromatography column after being spin-dried for solvent under reduced pressure, solvent is petroleum ether: chloroform (v:v=1:3) produces gained
Object recrystallizes in methylene chloride/methanol, and obtaining dark brown solid is compound C (66.9mg, 11.7%).
1H NMR(400MHz,Chloroform-d)δ9.19–8.84(m,8H),8.66(m,20H),8.28(m,16H),
7.93–7.69(m,10H),7.64(m,16H),6.26–4.79(m,8H),2.19m,16H),2.05–1.67(m,16H),
1.43–1.02(m,128H),1.01–0.46(m,48H),-2.67(s,2H).(MALDI-TOF)m/z 3961.2286(M+).
Embodiment 2
The synthesis of compound D provided in an embodiment of the present invention, reaction equation are as follows:
By compound C (61mg, 0.015mmol), zinc acetate (33mg, 0.15mmol), 15mL chloroform be added to
It in 100mL two mouth flask, is stirred at room temperature 4 hours, is spin-dried for solvent at reduced pressure conditions, purified in tlc silica gel plate, open up
Opening agent is petroleum ether: chloroform (v:v=1:3).Products therefrom is recrystallized in methylene chloride/methanol, obtains dark-brown
Solid and be compound D (56mg, 91%).
1H NMR(400MHz,Chloroform-d)δ9.28–8.89(m,8H),8.86–8.53(m,20H),8.44–
8.16(m,16H),7.86–7.69(m,10H),7.70–7.55(m,16H),5.27–4.83(m,8H),2.51–2.02(m,
16H),2.04–1.69(m,16H),1.47-0.98(m,128H),1.02–0.46(m,48H).13C NMR(101MHz,
Chloroform-d)δ147.86,146.21,145.15,142.86,142.41,141.40,138.71,137.39,136.01,
135.03,134.87,134.83,134.58,133.90,132.49,132.22,132.09,131.96,130.05,129.73,
129.33,128.56,128.21,127.69,126.56,125.85,123.59,123.09,122.67,121.30,54.80,
54.62,32.41,32.31,31.95,31.77,31.67,29.72,29.38,29.25,29.13,26.92,26.84,
22.71,22.60,22.51,14.14,14.06,13.98.(MALDI-TOF)m/z 4025.5513(M+)。
Porphyrin small organic molecule photovoltaic acceptor material manufactured in the present embodiment is dissolved in chloroform soln, obtains three chloromethanes
The uv-vis spectra of alkane solution is shown in Fig. 1.
Porphyrin small organic molecule photovoltaic acceptor material manufactured in the present embodiment is prepared into film, obtaining the ultraviolet of film can
Light-exposed spectrum is shown in Fig. 1.
The photovoltaic cell prepared using the porphyrin small organic molecule photovoltaic acceptor material of the present embodiment is at (AM 1.5)
100mW/cm2Current -voltage curve under illumination is shown in Fig. 2, device architecture ITO/PEDOT:PSS/ active layer/ZrAcac/Al.Institute
The device photoelectric transfer efficiency of preparation is 7.7%, open-circuit voltage 0.84V, short circuit current 14.53mA/cm2, fill factor
It is 62.7%.
In the following chemical structure of porphyrin small molecule photovoltaic acceptor material of the invention:
π is the triphenylamine or N- phenyl-carbazole π bridge for being connected to imidodicarbonic diamide, and A is imidodicarbonic diamide, M be hydrogen, copper from
Son, magnesium ion, iron ion etc., Ar can also be that other aromatic substituent groups, preparation principle and performance and the present invention provide
Embodiment is similar.
Fig. 3 is that porphyrin small organic molecule photovoltaic acceptor material prepared by embodiment 2 is used to prepare photovoltaic cell, photovoltaic cell
In AM 1.5,100mW/cm-2External quantum efficiency curve graph under illumination.
Below with reference to effect, the invention will be further described.
Branching porphyrin of the invention-imidodicarbonic diamide small organic molecule photovoltaic acceptor material improves the light capture energy of material
Power, and there is the complementary and level-density parameter of good absorption after combining with narrow band gap polymer donor material PTB7-Th etc.；It is higher
Molecular weight substantially improve the film forming of imidodicarbonic diamide, branched structure improves the pattern of active layer, by this micromolecular
Receptor is applied to organic solar batteries, can obtain the up to open-circuit voltage of 0.84V, 7.7% photoelectric conversion efficiency is filled
Divide and presents the corproporphyrin-imidodicarbonic diamide small molecule receptor in the application prospect in organic photovoltaic field
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by the embodiment
Limitation, it is other any away from made changes, modifications, substitutions, combinations, simplifications under spiritual essence and principle of the invention,
It should be included within the scope of the present invention with equivalent substitute mode.
Claims (10)
1. a kind of porphyrin-imidodicarbonic diamide organic molecule solar cell acceptor material, which is characterized in that the porphyrin-
Imidodicarbonic diamide organic molecule solar cell acceptor material has the organic sun of the non-fullerene of branching of the π bridge in multi-connection site
Energy battery acceptor material, general structure such as formula I:
Wherein: π is benzene, triphenylamine, the N- phenyl-carbazole, Tetrabenzene methane or four phenylsilane π for being connected to multiple imidodicarbonic diamide
Bridge；A is imidodicarbonic diamide；M is hydrogen or metal ion；Ar is hydrogen, alkyl, alkoxy, unsubstituted or substituted aromatic group.
2. porphyrin as described in claim 1-imidodicarbonic diamide organic molecule solar cell acceptor material, which is characterized in that
The π is benzene, triphenylamine, the N- phenyl-carbazole for being connected to multiple imidodicarbonic diamide, Tetrabenzene methane or four phenylsilane π bridges, for knot
One of 1~structural formula of structure formula 5:
3. porphyrin as described in claim 1-imidodicarbonic diamide organic molecule solar cell acceptor material, which is characterized in that
The Ar is hydrogen, and alkyl, alkoxy, one or more of unsubstituted or substituted aromatic heterocycle is 6~structural formula of structural formula 9
One of:
Wherein, R1With R2It is identical or different, for be 0-20 containing carbon number alkyl, alkoxy, it is for hydrogen that carbon, which is 0,.
4. porphyrin as described in claim 1-imidodicarbonic diamide organic molecule solar cell acceptor material, which is characterized in that
One of the A is structural formula 11)~structural formula 14):
5. porphyrin as described in claim 1-imidodicarbonic diamide organic molecule solar cell acceptor material, which is characterized in that
When the M is metal ion, metal ion is zinc ion, iron ion, nickel ion, magnesium ion, copper ion or iridium ion.
6. a kind of porphyrin as described in claim 1-imidodicarbonic diamide organic molecule solar cell acceptor material preparation side
Method, which is characterized in that the porphyrin-imidodicarbonic diamide organic molecule solar cell acceptor material preparation method include with
Lower step:
It is prepared using [2+2] synthetic method:,, will by catalyst system using organic solvent as reaction medium under atmosphere of inert gases
Even pyrroles reacts with aldehyde, and subsequent processing obtains porphyrin-imidodicarbonic diamide organic molecule solar cell acceptor material.
7. porphyrin as claimed in claim 6-imidodicarbonic diamide organic molecule solar cell acceptor material preparation method,
It is characterized in that, even the structural formula of pyrroles is formula II:
Formula II:
The structural formula of the aldehyde is formula III:
III: A- π-CHO of formula；
Wherein: the Ar even in the structure in pyrroles is identical as the Ar in porphyrin small organic molecule photovoltaic acceptor material structural formula I；Aldehyde
In structure in π and A in porphyrin small organic molecule photovoltaic acceptor material structural formula I π and A it is identical.
8. porphyrin as claimed in claim 6-imidodicarbonic diamide organic molecule solar cell acceptor material preparation method,
It is characterized in that, the organic solvent is dichloromethane or chloroform, and the catalyst system is trifluoroacetic acid；
The time of reaction is 8 hours；
The aldehyde is identical as the even mole of pyrroles, and the mole of trifluoroacetic acid is to connect pyrroles's mole in the catalyst system
10%.
9. porphyrin as claimed in claim 6-imidodicarbonic diamide organic molecule solar cell acceptor material preparation method,
Be characterized in that, the subsequent processing be reaction solution is cooling, wash, extraction is spin-dried for, then by chromatography, it is subsequent again
Metal coordination is carried out, chromatographic column is pure, is spin-dried for, and is dried in vacuo；
The extraction refers to that methylene chloride is extracted.
10. a kind of utilize porphyrin described in claim 1-imidodicarbonic diamide organic molecule solar cell acceptor material preparation
Full stress-strain solar battery.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111187271A (en) * | 2020-01-08 | 2020-05-22 | 华南理工大学 | Porphyrin organic small molecule receptor material, preparation method thereof and application thereof in organic solar cell |
| CN113461715A (en) * | 2021-07-30 | 2021-10-01 | 南京林业大学 | Tetraperylene diimide based phenyl tetraphenanthrene ring conjugated porphyrin derivative and preparation method thereof |
| CN113666949A (en) * | 2021-08-30 | 2021-11-19 | 陕西师范大学 | Gold (III) complex-perylene diimide derivative and fluorescent sensing tube and tubular fluorescent sensor prepared from same |
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| ANDONG ZHANG，等: "An Electron Acceptor with Porphyrin and Perylene Bisimides for Efficient Non-Fullerene Solar Cells", 《ANGEW. CHEM.》 * |
| MARK O. LIU，等: "The fluorescent and photoelectric conversion properties of porphyrin–perylene tetracarboxylic complex", 《JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A: CHEMISTRY》 * |
| TAMAR VAN DER BOOM，等: "Charge Transport in Photofunctional Nanoparticles Self-Assembled from Zinc 5,10,15,20-Tetrakis(perylenediimide)porphyrin Building Blocks", 《J. AM. CHEM. SOC.》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111187271A (en) * | 2020-01-08 | 2020-05-22 | 华南理工大学 | Porphyrin organic small molecule receptor material, preparation method thereof and application thereof in organic solar cell |
| CN113461715A (en) * | 2021-07-30 | 2021-10-01 | 南京林业大学 | Tetraperylene diimide based phenyl tetraphenanthrene ring conjugated porphyrin derivative and preparation method thereof |
| CN113666949A (en) * | 2021-08-30 | 2021-11-19 | 陕西师范大学 | Gold (III) complex-perylene diimide derivative and fluorescent sensing tube and tubular fluorescent sensor prepared from same |
| CN113666949B (en) * | 2021-08-30 | 2022-07-12 | 陕西师范大学 | Gold (III) complex-perylene diimide derivative and fluorescent sensing tube and tubular fluorescent sensor prepared from same |
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| CN110143976B (en) | 2021-11-02 |
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