TR201415962A2 - Electroactive monomers containing polyhedral oligomeric silsesquoxane. - Google Patents
Electroactive monomers containing polyhedral oligomeric silsesquoxane. Download PDFInfo
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- TR201415962A2 TR201415962A2 TR2014/15962A TR201415962A TR201415962A2 TR 201415962 A2 TR201415962 A2 TR 201415962A2 TR 2014/15962 A TR2014/15962 A TR 2014/15962A TR 201415962 A TR201415962 A TR 201415962A TR 201415962 A2 TR201415962 A2 TR 201415962A2
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- 239000000178 monomer Substances 0.000 title claims description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229930192474 thiophene Natural products 0.000 claims abstract description 6
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000002776 aggregation Effects 0.000 claims description 6
- 238000004220 aggregation Methods 0.000 claims description 6
- ILMNSCQOSGKTNZ-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)-2-oxoethoxy]-3-hydroxypropanal Chemical compound NC1=NC=NC2=C1N=CN2C(OC(CO)C=O)C=O ILMNSCQOSGKTNZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 abstract description 16
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 3
- 239000011263 electroactive material Substances 0.000 abstract description 2
- 238000010276 construction Methods 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920002098 polyfluorene Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical class O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229920001746 electroactive polymer Polymers 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000005868 electrolysis reaction Methods 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZUDCKLVMBAXBIF-UHFFFAOYSA-N 3,4-dimethoxythiophene Chemical compound COC1=CSC=C1OC ZUDCKLVMBAXBIF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YHEBYTAHDOHSHQ-UHFFFAOYSA-N 2-piperidin-1-yl-1-selenophen-2-ylethanol Chemical compound C=1C=C[se]C=1C(O)CN1CCCCC1 YHEBYTAHDOHSHQ-UHFFFAOYSA-N 0.000 description 1
- IEXLMWZQCURUMB-UHFFFAOYSA-N 3-acetyl-1-(dimethylamino)-4,4a,6,7,11,12-hexahydroxy-11-methyl-1,11a,12,12a-tetrahydrotetracene-2,5-dione Chemical compound C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(=O)C(C(C)=O)=C(O)C4(O)C(=O)C3=C(O)C2=C1O IEXLMWZQCURUMB-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 208000022379 autosomal dominant Opitz G/BBB syndrome Diseases 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- CJUDSKIRZCSXJA-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 CJUDSKIRZCSXJA-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Mevcut buluş, elektroaktif bir bileşiğin polihedral oligomerik silseskuokzan (POSS) ile yeni bir elektroaktif bileşik oluşturması sonucu çözünür olmayan poli(3,4-alkilendioksi-[tiyofen, selenofen, pirol, furan veya tellurofen]) (PADOX) polimerleri gibi elektroaktif malzemelerin çözünür ve kararlı bir polimerik yapı haline getirilerek, yeni polimerik yapının farklı kaplama yöntemleri ile istenilen yüzeye kaplanabilmelerinin mümkün kılınması, yeni polimerik malzemelerin sentezinde, yeni bileşiklerin eldesi sırasında bir entegre parça olarak veya ışık saçan diyot (LED), güneş pili, elektrokromik cam, transistör vb. yapımında kullanılabilmesinin sağlanması ile ilgilidir.The present invention relates to the dissolution of electroactive materials, such as poly (3,4-alkylenedioxy- [thiophene, selenophene, pyrrole, furan, or tellurofen]) (PADOX) polymers, resulting in the formation of a novel electroactive compound with an by making the polymeric structure a stable polymeric structure, enabling the new polymeric structure to be coated to the desired surface by different coating methods. to ensure that it can be used in construction.
Description
TARIFNAME POLIHEDRAL OLIGOMERIK SILSESKUOKZAN IÇEREN ELEKTROAKTIF MONOMERLER Bulusun ilgili Oldugu Teknik Saha Mevcut bulus, elektroaktif bir bilesigin polihedral oligomerik silseskuokzan (POSS) ile yeni bir elektroaktif bilesik olusturmasi sonucu çözünür olmayan poli(3,4-alkilendioksi-[tiyofen, selenofen, pirol, furan veya tellurofen]) (PADOX) polimerleri gibi elektroaktif malzemelerin çözünür ve kararli bir polimerik yapi haline getirilmesi ile ilgilidir. DESCRIPTION ELECTROACTIVE MONOMERS CONTAINING POLYHEDRAL OLIGOMERIC SILSESKUOKZAN Technical Field of the Invention The present invention is a novel invention of an electroactive compound with polyhedral oligomeric silsesquoxane (POSS). insoluble poly(3,4-alkylenedioxy-[thiophene, of electroactive materials such as selenofen, pyrrole, furan or tellurofen]) (PADOX) polymers. It is about making a soluble and stable polymeric structure.
Teknigin Bilinen Durumu Polihedral oligomerik silseskuokzan (POSS) gruplarinin organik fonksiyonel gruplari istenilen amaca göre tasarlanip istenilen sekilde polimer zincirine eklenebilmektedir. POSS gruplarinin eklendigi matrikse termal ve mekanik özellikler kattigi bilinmektedir. State of the Art The organic functional groups of polyhedral oligomeric silsesquoxane (POSS) groups are the desired It can be designed according to the purpose and added to the polymer chain as desired. POSS groups It is known that it adds thermal and mechanical properties to the matrix to which it is added.
Kismen iyi islenebilirlikleri ve yüksek floresan kuantum verimleri nedeniyle isik saçan diyot (LED) uygulamalar için elektroaktif polimerler üzerine oldukça fazla arastirma yapilmaktadir. Light-emitting diode, partly due to its good machinability and high fluorescent quantum yields Much research is being done on electroactive polymers for (LED) applications.
Fakat elektroaktif polimerler, cihaz üretimi ve çalismasi sirasinda kümelenme ve/veya zincirarasi eksimerler olusturma egilimindedirler. Buna ek olarak, polimer omurgasi termal olarak kararsizdir. Örnegin polifuloren keto etkiden dolayi yesil emisyon göstermektedir. However, electroactive polymers may cause aggregation and/or aggregation during device fabrication and operation. they tend to form interchain excimers. In addition, the polymer backbone is thermally as undecided. For example, polyfluorene shows green emission due to the keto effect.
Kümelenme olusumunu azaltmak ve termal dayanimi arttirmak için POSS grubunun polifulorenlere sondan bagli ve yan zincirler olarak katildigi ve POSS/polifuloren esasli elektrolüminesan cihazlarin (LEDIer) sadece polifuloren içerenlere göre iki kat daha iyi oldugu görülmüstür (Lin, W.-J.; Chen, W.-C.; Wu, W.-C.; Niu, Y.-H.; Jen, A.K.-Y., Macromolecules, 37, 2335, 2004). To reduce aggregation and increase thermal resistance, POSS group POSS/polyfluorene-based Electroluminescent devices (LEDs) are twice as good as those containing only polyfluorene. (Lin, W.-J.; Chen, W.-C.; Wu, W.-C.; Niu, Y.-H.; Jen, A.K.-Y., Macromolecules, 37, 2335, 2004).
Formül I'de verilen polimer, yildiz yapisinda bir polifuloren türevidir. Bahsi geçen çalismalarda POSS grubunun polifuloren içerisine katkilandirilmasinin kümelenmeyi önemli Ölçüde düsürdügü gibi termal dayanimi da arttirdigi görülmüstür. POSS grubu içeren polimerin 150°C'da dahi fotolüminesans spektrumu gözlenebilmistir. POSS grubunun bulunmadigi polifuloren ise ayni sicaklikta mavi isik ile beraber 530 nanometrede kayda deger bir yesil emisyon göstermistir. POSS grubu içeren polimer ile hazirlanmis tek katli bir LED cihazi açilis degerlerini göstermistir. POSS grubu içeren polimerin en yüksek Iüminesans yogunlugu ve kuantum verimi polifuloren elektrolüminesan cihazina göre iki kat olmustur. › gr ;9 `s- "E 3:? %5. I: &I :1 ?xx !a EH 'i g. . `i've-M fx““w'gü .. :I "I g. !i ;? %4?` esi? ““13 :g: :42?` E meze R::: _ - M** E" sunma& î?... mâ, 5:* JT" I Er fm 2' K.? Ö `si-msj `VT-*KM »[3 fe i 7 ...muz ya.” _3 SF *~ g: *Iv- 4& 5 ”Na ,YL M :I L w .. `f' 92%“ ,55”, i`ll Is mm; y Ü Wj' “her“, x , - `i s Formül I Ayni sekilde kuartz film üzerinde, Formül II'de verilen polimerin fotolüminesans spektrumlari, hacimli POSS gruplari zincirler arasi etkilesimi engelledigi için, düsük kümelenme/eksimer olusumu göstermislerdir. Ayrica bu polimeri kullanarak yapilan elektrolüminesan cihaz oldukça dayanikli mavi isik emisyonu göstermistir. Bu LED cihazlari 3,7 - 4,4 V gibi düsük açilis H3C'SE'CH3 ch-Si-Q C? Hac POSS POSS Formül II POSS grubunun yukarida bahsi geçen endüstriyel malzemelerde kullanilmasi ve gerek kimyasal gerekse fiziksel özelliklerini iyilestirmesi, bu gruplara olan ilgiyi daha da artirmistir. The polymer given in formula I is a star-shaped polyfluorene derivative. In the aforementioned studies Doping POSS group into polyfluorene significantly reduced aggregation. It has been seen that it increases the thermal resistance as well as reduces the temperature. Polymer containing POSS group Photoluminescence spectrum could be observed even at 150°C. No POSS group On the other hand, polyfluorene is a remarkable green at 530 nanometers with blue light at the same temperature. showed no emissions. Opening a single layer LED device prepared with polymer containing POSS group. did not show their values. The highest luminescence density of the polymer containing POSS group and The quantum yield was twice that of the polyfluorene electroluminescent device. › gr ;9 `s- "E 3:? 5%. I: &I :1 ?xx !a EH i g. . `i've-M fx““w'gü .. :I "I g. !i ;? %4?` esi? ““13 :g: :42?` E appetizer R::: _ - M** E" present& î?... mâ, 5:* JT" I Er fm 2' K.? Ö `si-msj `VT-*KM »[3 fe i 7 … bananas.” _3 SF *~ g: *Iv- 4& 5 ”Na ,YL M :I L w .. `f' 92%“ .55”, i`ll Is mm; y Ü Wj' “every“, x , - `i s Formula I Likewise, on the quartz film, the photoluminescence spectra of the polymer given in Formula II, low aggregation/excimer, as bulky POSS groups prevent inter-chain interaction They showed the formation. In addition, electroluminescent device made using this polymer It showed very stable blue light emission. These LED devices are low power-on, such as 3.7 - 4.4 V. H3C'SE'CH3 ch-Si-Q C? Hajj POSS POSS Formula II The use of the POSS group in the above-mentioned industrial materials and The improvement of their chemical and physical properties has further increased the interest in these groups.
Bu ilgi POSS gruplarinin elektrokromik polimerlerde de kullanilabilmesinin yolunu açmistir. This interest has paved the way for the use of POSS groups in electrochromic polymers.
Polianilin üzerine yapilan çalismalar (Xiong, S.; Xiao, Y.; Ma, J.; Zhang, L.,' Lu, X., Macromol. tipi kopolimerlerin, polianiline oranla daha iyi bir iyon iletkenligine sahip oldugunu göstermistir ki kopolimerlerin optiksel renk kontrasinin polianiline oranla yaklasik %40 daha iyi oldugu bilinmektedir. Sema I'de görülmektedir ki kopolimerler içerisindeki POSS gruplari zincirler arasindaki mesafeyi artirarak, iyon giris-çikisini daha da kolaylastirmistir. Studies on polyaniline (Xiong, S.; Xiao, Y.; Ma, J.; Zhang, L.,' Lu, X., Macromol. type copolymers have a better ion conductivity than polyaniline. showed that the optical color contrast of the copolymers was approximately 40% lower than that of polyaniline. It is known to be good. It can be seen in Scheme I that POSS groups in copolymers By increasing the distance between the chains, it has made the ion entry-exit easier.
Sema II'de gösterilen bir baska çalismada (Ak, M.; Gacal, B.; Kiskan, B.; Yagci, Y.; Toppare, L., homopolimeri elde etmek mümkün olmamistir. Pirol ile beraber elde edilen kopolimerin ise polipirole oranla optiksel zitlik oraninin arttigi ve daha hizli bir anahtarlama süresine sahip oldugu görülmüstür. In another study shown in Sema II (Ak, M.; Gacal, B.; Kiskan, B.; Yagci, Y.; Toppare, L., It was not possible to obtain the homopolymer. The copolymer obtained with pyrrole It has an increased optical contrast ratio and a faster switching time compared to polypyrrole. it has been seen.
N' : ,srçwßksiig Ç) ;away-»si EDOT türevlerinin elektrokromik malzemelerde çok kullanilir olmasinin baslica sebebi, farkli potansiyeller altinda göstermis oldugu optik zitlik ve tersinirliktir (nötr hali: koyu mavi (lacivert); yükseltgen hali: seffaf mavi, A%T=%52). Ayrica bu monomerler daima ayni yerden dogrusal olarak polimerlesirler. Ne var ki, EDOT'dan elde edilen polimerlerin yaygin çözücülerde çözünmüyor olusu ve anahtarlanma süresinin 2-2,5 sn arasi olmasi bir dezavantaj olarak görülmektedir. EDOT (3,4-etilendioksitiyofen) birimi kullanilarak elde edilen polimerlerin bir kisminin termal ve elektrokimyasal kararliliklari zayiftir ve de açik hava ortamina karsi istenilen uzun ömürlü dayanimi gösteremezler. Ayrica bu polimerler istenilen renk kontrasti, hizli anahtarlanma ve renk etkinligini de gösteremezler. N' : ,srçwßksiig C) ;away-»si The main reason why EDOT derivatives are widely used in electrochromic materials is that different optical contrast and reversibility under potentials (neutral state: dark blue) (navy blue); oxidizing state: transparent blue, A%T=52%). Also, these monomers are always from the same place. they polymerize linearly. However, polymers from EDOT are widely It is a disadvantage that it is insoluble in solvents and the switching time is between 2-2.5 seconds. is seen as. Obtained using the EDOT (3,4-ethylenedioxythiophene) unit The thermal and electrochemical stability of some of the polymers is poor and also in the open air. they cannot show the desired long-lasting resistance against the environment. In addition, these polymers Nor can they show color contrast, fast switching and color efficiency.
Bulusun Amaci Mevcut bulusun amaci, bilinen elektroaktif polimerlere oranla daha üstün özelliklere sahip daha özel bir ifade ile çözünürlük, termal, renk (optiksel) ve elektrokimyasal kararsizlik gibi bir takim temel sorunlardan arindirilmis, polihedral oligomerik silseskuokzan (POSS) içeren bir elektroaktif monomerin temin edilmesidir. Purpose of the Invention The object of the present invention is to have superior properties compared to known electroactive polymers. more specifically, solubility, thermal, color (optical) and electrochemical instability. The team is based on a defect-free, polyhedral oligomeric silsesquioxane (POSS). supply of electroactive monomer.
Mevcut bulusun diger bir amaci, elektroaktif polimer olarak adlandirilan ve çözünür olamayan PADOX (PADOT, PADOS, PADOP, PADOF, PADOTe) (poli(3,4-aIkilendioksi-[tiyofen, selenofen, pirol, furan, tellurofen])) gibi polimerlerin, polihedral oligomerik silseskuokzan (POSS) ile entegrasyonu sonrasinda çözünür ve kararli polimerik yapilar haline getirilerek, farkli kaplama yöntemleri ile istenilen yüzeye kaplanmalarini mümkün kilmaktir. Another object of the present invention is the so-called electroactive polymer, which is an insoluble PADOX (PADOT, PADOS, PADOP, PADOF, PADOTe) (poly(3,4-alkylenedioxy-[thiophene, selenophene, pyrrole, furan, tellurofen])) with polyhedral oligomeric silsesquoxane (POSS) After integration, they are made into soluble and stable polymeric structures and different coating It is to enable them to be coated on the desired surface with methods.
Bulusun Açiklamasi Mevcut bulus, polihedral oligomerik silseskuokzan içeren elektroaktif monomer, üç ana kisimdan meydana gelmektedir. ADOX olarak tanimlanan birim Formül III'te X elementinin yerine gelecek olan 5, Se, NH, 0, Te göre degisiklik göstermekte ve sirasiyla ADOT, ADOS, ADOP, ADOF, ADOTe olarak adlandirilmaktadir. Description of the Invention The present invention is an electroactive monomer containing polyhedral oligomeric silsesquoxane, three main comes from the person. The unit defined as ADOX is in Formula III of element X. 5, Se, NH, 0, Te, which will replace it, and ADOT, ADOS, It is called ADOP, ADOF, ADOTe.
ADOX (3,4-alkilendioksi-[tiyofen, selenofen, pirol, furan ve tellurofen]) birimi polimerlesmenin gerçeklesebilecegi birim olup, polihedral oligomerik silseskuoksan (POSS) grubu ise elde edilecek polimerin üzerinde bulunan gruplar sayesinde hem çözünür hem de elektrokimyasal, kimyasal ve termal olarak kararli olmasini saglayacak birimdir. Üçüncü kisim ise ADOX ve POSS arasindaki birim olup makul polimerlesme için gerekli zincir uzunlugudur. The ADOX (3,4-alkylenedioxy-[thiophene, selenophene, pyrrole, furan and tellurofen]) unit It is the unit where it can be realized, and the polyhedral oligomeric silsesquoxane (POSS) group can be obtained. Thanks to the groups on the polymer to be made, it is both soluble and electrochemical, It is the unit that will ensure that it is chemically and thermally stable. The third part is ADOX and POSS is the chain length required for reasonable polymerization.
Bulus konusu bilesige ait üç ana kisim Formül III'te gösterilmistir ve Formül III'te; R1 her defasinda -H, ~CnHizn+i), -CnHZnOCnHuMn, -OSi(Me)2, -CH(CnH(2n+1))2 veya -C(CnH(2n,1))3 R2 her defasinda -CnH(2n,-, -O-, -Si(Me)2- veya -CnHZnOCnH(2n)- R3 her defasinda -CnH2n-1- X ise her defasinda S, Se, NH, 0 veya Te temsil eder. Three main parts of the subject compound are shown in Formula III and in Formula III; R1 each time -H, ~CnHizn+i), -CnHZnOCnHuMn, -OSi(Me)2, -CH(CnH(2n+1))2 or -C(CnH(2n,1))3 R2 is always -CnH(2n,-, -O-, -Si(Me)2- or -CnHZnOCnH(2n)- R3 every time -CnH2n-1- X each time represents S, Se, NH, 0 or Te.
POSS sir» `/sii Ara Zincir Formül III Tepkimenin gerçeklesecegi düzenek; o Yogunlastiriciya bagli bir soxhlet ekstraktöre ve ona bagli yag banyosunun içerisinde iki boyunlu bir tepkime balonu içerisinde gerçeklestirilir. o Soxhlet ekstraktörünün içerisinde 3 Ã gözenek boyutuna sahip moleküler elek önceden isitilip kurutulduktan sonra yerlestirilir. 112 oraninda 3,4-dimetoksitiy0fen ve diollü POSS grubu, argon gazi altinda tolüen çözücüsü içerisinde çözünür. Çözeltinin içerisine 3,4-dimetoksitiyofen miktarinin molce onda biri kadar para-tolüensülfonik asit eklenir. Daha sonra tepkime çözeltisi oda sicakligindan 120°C'a kadar isitilir, manyetik karistirici ile karisitirilir ve reflaks olmasi saglanir. Tepkime 96 saat boyunca reflaks olduktan sonra tepkime çözeltisi içerisindeki tüm çözücü uçurulur. Kalan kati kisim diklorometan çözücüsü içerisinde çözülür ve üzerine diklorometan miktarinca su eklenir. POSS sir» `/si Intermediate Chain Formula III The mechanism in which the reaction will take place; o In a soxhlet extractor connected to the concentrator and in the oil bath connected to it, two carried out in a necked reaction balloon. o Inside the Soxhlet extractor, a molecular sieve with a pore size of 3 Ã placed after heating and drying. POSS group with 112 ratio of 3,4-dimethoxythiophene and diol, toluene solvent under argon gas dissolves in One tenth of the mole amount of 3,4-dimethoxythiophene into the solution para-toluenesulfonic acid is added. Then the reaction solution is heated from room temperature to 120°C. It is heated, mixed with a magnetic stirrer and reflux is ensured. Reaction for 96 hours After reflux, all solvent in the reaction solution is evaporated. remaining solid It is dissolved in dichloromethane solvent and water is added in the amount of dichloromethane.
Karisim ayirma hunisi içerisine konulur. Daha sonra diklorometan fazi karisim içerisinden ayrilir. Bu islem ayni miktar diklorometan ile 2 kez daha yapilir ve toplanan diklorometan bir miktar MgSO4 ile kurutulur. Filtre ediltikten sonra çözücünün tamami uçurulur. Süzme kolonu, hekzanzetilasetat çözücü karisimi kullanilarak yapilir ve malzemenin içerisindeki istenmeyen tüm yan ürünler ayrilip, ürün toplanir. Son olarak çözücünün tamami uçurulur. The mixture is put into the separating funnel. Then the dichloromethane phase is mixed through the mixture. are separated. This process is done 2 more times with the same amount of dichloromethane and the collected dichloromethane is collected. amount is dried with MgSO4. After filtration, all the solvent is evaporated. filtration column, It is made using a solvent mixture of hexanzetylacetate and removes unwanted all by-products are separated and the product is collected. Finally, all of the solvent is evaporated.
Sentez sirasinda, toluen yerine tetrahidrofuran kullanilarak tepkimenin daha uzun sürede, daha düsük sicaklik degerinde (70°C civari) gerçeklesmesi saglanabilir. During the synthesis, by using tetrahydrofuran instead of toluene, the reaction takes longer time, It can be achieved at a lower temperature value (around 70°C).
Formül IV ile gösterilen ve EDOT- POSS olarak adlandirilan monomer Formül III'te verilen iskelet yapida; X yerine 5 elementi, R1 yerine izobütil grubu (-CH2CH(CH3)2), R2 yerine (-CH2-CH2- CHz-O-CH2-) grubu, R3 yerine (-C-) R4 yerine ise (-H) kullanilarak elde edilebilir. The monomer denoted by Formula IV and named EDOT-POSS is given in Formula III. in skeletal structure; 5 element instead of X, isobutyl group (-CH2CH(CH3)2) instead of R1, (-CH2-CH2-CH2-O-CH2-) group instead of R2, (-C-) instead of R3 It can be obtained by using (-H) instead of R4.
Formül IV Formül V ile gösterilen ve ProDOT-POSS olarak adlandirilan monomer ise Formül III'te verilen iskelet yapida; X yerine 5 elementi, R1 yerine izobütil grubu (-CH2CH(CH3)2), R2 yerine (-O-Si(CH3)2-CH2-CH2- CHz-O-CH2-) grubu, R3 yerine (-CH2-C~) R4 yerine ise (-CHZ-CH3) kullanilarak elde edilebilir. Formula IV The monomer represented by Formula V and named ProDOT-POSS is given in Formula III. in skeletal structure; 5 element instead of X, isobutyl group (-CH2CH(CH3)2) instead of R1, (-O-Si(CH3)2-CH2-CH2- CH2-O-CH2-) group instead of R2, instead of R3 (-CH2-C~) It can be obtained by using (-CH2-CH3) instead of R4.
Formül V Formül IV ve Formül V ile verilen iki örnek elektroaktif monomerler, Formül III'te verilmis olan iskelet yapida, yukarida anlatilmis olan tepkime metodu ile sentezlenebilmektedir. Formula V Two exemplary electroactive monomers with Formula IV and Formula V are given in Formula III. It can be synthesized by the reaction method described above in the skeleton structure.
Bulus konusu elektroaktif monomer, elektrokimyasal çalismalarda elde edilen yükseltgenme potansiyel degerlerinde yapilan elektrolizler (sabit potansiyel elektrolizi, sabit akim elektrolizi ve taramali potansiyel yöntemleri) ile elektroaktif homopolimer veya farkli bilesiklerinde (3,4- etilendioksitiyofen, pirol, tiyofen vb.) bulundugu ortam sartlari kullanilarak kopolimer elde edilebilmesine açiktir. The subject of the invention is the electroactive monomer, the oxidation obtained in electrochemical studies. electrolysis at potential values (constant potential electrolysis, constant current electrolysis and scanning potential methods) and electroactive homopolymer or different compounds (3,4- ethylenedioxythiophene, pyrrole, thiophene etc.) to obtain copolymer by using ambient conditions. open to possible.
Polimerlesme elektrokimyasal yöntemlerin yani sira kimyasal yöntemlerle de saglanabilmektedir. Kimyasal polimerizasyon Stille, Suzuki eslesmelerinin yani sira susuz FeCl3 kullanilarak da yapilabilmektedir. Elde edilen polimer, metanol yardimi ile çöktürülüp Soxhlet geri-dönüsümlü sogutucusu ile yikanip tekrar metanolde çöktürülüp kurutulur. Polymerization can be done by chemical methods as well as electrochemical methods. can be provided. Chemical polymerization Stille, Suzuki matches as well as anhydrous FeCl3 It can also be done using The resulting polymer was precipitated with the help of methanol and the Soxhlet washed with a recycle cooler, precipitated again in methanol and dried.
Bulusun Sanayiye Uygulanma Biçimi Yukarida bahsedilen amaçlara hizmet eden polihedral oligomerik silseskuokzan (POSS) içeren elektroaktif bilesik, çözünür ve kararli bir polimerik yapi olup PADOX (poli(3,4-alkilendi0ksi- farkli kaplama yöntemleri ile istenilen yüzeye kaplanmalarini mümkün kilmakta, yeni polimerik malzemelerin sentezinde, yeni bilesiklerin eldesi sirasinda bir entegre parça olarak veya isik saçan diyot (LED), günes pili, elektrokromik cam, transistör vb. yapiminda kullanilabilir nitelikte olup sanayiye uygulanabilir yapidadir. Industrial Application of the Invention containing polyhedral oligomeric silsescuoxane (POSS) serving the above-mentioned purposes. The electroactive compound is a soluble and stable polymeric structure, PADOX (poly(3,4-alkylenedioxy- It makes it possible to cover the desired surface with different coating methods, As an integral part in the synthesis of polymeric materials, during the production of new compounds or light-emitting diode (LED), solar cell, electrochromic glass, transistor, etc. in the making It is usable and industrially applicable.
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