KR100534077B1 - Compound of farnesyl and dendrimer - Google Patents

Abstract

The present invention is to provide a composite of a dendrimer (dendrimer) containing farnesol widely used as a light emitting device, a DNA-support, RNA-hydrolysing derivatives, etc. as a new compound of the multifunctional dendrimer.

That is, the present invention binds farnesol to the outermost surfaces of the first, second, third and fourth generation carbosilane dendrimers, and thus is a composite of dendrimers containing 12, 36, 108 and 324 farnesyl groups, respectively. In addition, a low cost model was synthesized through the introduction of a siloxane polymer Me ₃ SiO (MeRSiO) _n SiMe ₃ (R = added dendrimer) as a nuclear molecule. In order to improve sex, dendrimerized siloxane polymer was developed to have 3, 6 and 9 farnesyl functional groups per unit cell. This ideal binding type was confirmed by NMR, IR and UV spectroscopy, elemental analysis, and Maldi-mass method, and the purity was determined by GPC.

Description

Farnesyl dendrimer composite {Compound of farnesyl and dendrimer}

The present invention relates to a farnesyl dendrimer composite, and more particularly, one of the prior art is added by adding farnesyl functional groups having three double bonds on the surface of the dendrimer, which are being actively studied for application development. To provide a panesyl dendrimer composite provided by the new method of dendrimer synthesis, which confirms that only one functional group can be added to a dendrimer branch, and that several functional groups can be introduced into one branch. It is.

Introduction of a multifunctional functional group as in the present invention has not been found in any conventional dendrimer synthesis method, and such a process has not been introduced in the application of dendrimers known to date.

A general method for synthesizing siloxane oxime dendrimers has been disclosed and patented by the present inventors by introducing allyl functional groups or introducing allyloxy functional groups.

[Reference]:

1.Preparation, Identification And Application Of Dendritic Carbosilanes, C. Kim, Phosphorus Sulfur And Silicone And The Related Elements, 168 (2001) 339-340.

2.End-Capped Carbosilane Dendrimer, Hyperbranched Polymer And Staff-Type Dendritic Polymer, Macromolecular Chemistry Symposium Series (Synthesis And Application Of Advanced Polymeric Materials), 14 (2001) 20-28.

3. S. B. Jung, S.-Y. Yoo, Y.-S. Kwon, E. Park, C. Kim, Electrical Properties And Fabrication Of Dendrimer Lb Films Containing 48 Pyridinealdoxime Functional End Groups, J. Korea Phy. Soc., 40 (2002) 132-135.

4. C. Kim, H. Kim, Synthesis And Characterization Of End-Functionalized Carbosiloxane Dendrimers, J. Polym. Sci. A: Polym. Chem., 40. (2002) 326-333.

5. C. Kim, K. Kwark, Staff-Type Dendrimer: End-Functionalization Of Dendronized Siloxane Polymer Me3SiO- (MeSiHO) N-SiMe3, J. Polym. Sci. A: Polym. Chem., 40. (2002) 976-982.

6.C. Kim, B. W. Koo, S. B. Lee, C. K. Song, Conducting Behavior Of Carbosilane Dendrimers Including Palladium Ions, Macromolecular Research 10 (2002) 178-180.

7. C. Kim, K. Kwark, Pyridine End-Functionalized Polysiloxane Dendrimer, Main Group. Met. Chem. 25 (2002) 473-476.

8. C. Kim, H. Kim, Crown-Ether End-Capped Carbosiloxane Dendrimers, Bull. Korean Chem. Soc. 23 (4) (2002) 637-639.

9. C. K. Song, B. W. Koo, C. Kim, Application Of Dendrimer As A New Material For Electrical And Optical Devices, J. Appl. Phys. 41 (2002) 2735-2738.

10. T. Y. Lee, E. Park, B.-J. Lee, E. M. Son, C. Kim, Y.-S. Kwon, Monolayer Properties of a 4-Pyridinealdoxime-Containing Carbosilane Dendrimer, Mol. Cryst. Liq. Cryst. 377 (2002) 161-164.

11.E. Park, E. M. Son, B.-J. Lee, C. Kim, A Silyl Ether Network Langmuir-Blodgett Film from a Carbosilane Dendron, KIEE International Transactions on EA, 12C-1 (2002) 38-41.

12. C. Kim, I. Jung, C. K. Song, B. W. Koo, End-Capped Dendritic Ethynylsilane With Ferrocene, Amine And Pyridine Derivatives, Main Group Met. Chem. 25 (2002) 561-565.

13. C. Kim, K. Kwark, Dehydrocoupling And Diels-Alder Reaction On Siloxane Polymer, J. Polym. Sci. A: Polym. Chem. 40 (2002) 4013-4019.

14. C. Kim, H. Kim, 2,2: 6,2-Terpyridine And Bis (2,2,: 6,2-Terpyridine) Ruthenium Complex On The Dendritic Periphery, J. Organomet. Chem., 673 (2003) 77-83.

15. C. Kim, H. Kim. K. Park, Diels-Alder Reaction of Anthracene and N-ethylmaleimide on the Carbosilane Dendrimer, J. Organomet. Chem., 667 (2003) 96-102.

16. C. Kim, Organosilicone based dendrimer, Poly. Sci. & Tec., 13, (2002) 623.

Dendrimers generally have a spherical structure, and in the case of dendrimers developed on siloxane polymers, they have a staple type structure. In the present invention, the dendrimers have a polyfunctionality on the surfaces of these two types of dendrimers. function) The compound was designed to have functional groups formed on the surface of the dendrimer significantly improved than the number of branches.

Farnesol introduced in the present invention also has three functional double bonds in one molecule. The present inventors synthesized the first to fourth generations by adding farnesyl functional groups to the surface of the carbosilane dendrimer, and this synthesis method can be developed into a new method that can drastically change the method of dendrimer synthesis. The dendrimer produced by the synthesis method may have a multifunctional functional group on its surface.

In order to change the chemical process more quickly and easily by modeling the compound, a study of dendrimers based on siloxane polymers has been developed by the present inventors as a staff type dendrimer, and 9 farnesyl functional groups are added based on this shape. It was also synthesized up to the second generation compound.

The synthesis of these staff dendrimers can be applied to the synthesis of models that do not require exact molecular weight.

The technical problem to be achieved in the present invention is summarized as follows.

1. Synthesis of Carbosilane Dendrimers with Farnesyl Function (G1-12Far, G2-36Far, G3-108Far, G4-324Far) and Identification of Compounds

2. Introduction of farnesyl functional group on siloxane polymer

3. Synthesis of rod farnesyl dendrimer.

The present invention completes the present invention for the purpose of developing a technology that makes the application easier to apply the technical problems of the above 1-3.

The present invention is to form a skeleton structure of carbosilane dendrimer by the reaction of silane and allyl alcohol to synthesize the dendrimer from the first generation to the fourth generation compound to add farnesol to the surface of the dendrimer, Invented a method of dendrimerization using a siloxane polymer which is an easy synthesis method, but the terminal function is changed to a farnesyl functional group, although the precision of the product is inferior.

The Si-Cl bond added to the surface of each generation, which is the backbone of this reaction, could be achieved through hydrosilation reaction under HMe _3-n SiCl _n (n = 1 ~ 3) and platinum catalyst. Was obtained by combining farnesol here.

This reaction has almost 100% yield and the product has a very high purity and the yield tends to decrease with increasing generation of dendrimers, but this is only a problem in handling process and the actual degree of synthesis is not monitored on NMR. There was no side reaction, indicating that the reaction proceeds in a very high yield.

The present invention synthesizes farnesyl dendrimers from first generation to fourth generation and introduces the same method on siloxane polymer to synthesize staff type dendrimers.

Here, the synthesis of the Gn-mCl generation, which is the basis of each generation, was synthesized by the same method as the contents published in the paper by the present inventor.

The above formula is a process for synthesizing Gn-mFar, which means that n-generation (n = 1-4) dendrimers have m farnesyl (Far) groups (m = 12, 36, 108, 324), for example, For example, each generation means that the first generation (G1-12Far) has 12 farnesyl functional groups.

The present invention synthesized Dendrimer-SiCl ₃ in order to synthesize the material represented by the formula 1 and reacted in the presence of farnesol and TMEDA was purified by column chromatography.

The dendrimer formed in Chemical Formula 1 is very pure and has high purity, so that the reaction product is easily confirmed by NMR.

Hereinafter, various embodiments of the present invention will be described in more detail below.

(Example 1)

(Molecular)

The above formula is a dendrimer with farnesyl functional groups, which has a siloxane tetramer in the center and synthesizes double bonds in the end groups of the siloxane functional groups by adding four new SiCl ₃ functional groups by hydrosylation method and reacting with farnesol and the functional dendrimer. Substantial synthesis method of the above compound is as follows.

238 g of farnesol and 115 g of TMEDA were dissolved in 2.5 L of toluene in 65 g (74 mmol) of G1P-12Cl and slowly added thereto, followed by stirring for 2 hours.

After confirming the completion of all reactions by ¹ H NMR, HCl-TMEDA salt formed during the reaction was filtered off by adding pentane, and then all solvents and TMEDA added by vacuum distillation were removed.

The remaining farnesol and TMEDA were removed by column-chromatography using silica-gel and toluene, and the solvent was removed again by distillation under reduced pressure to obtain 194g (83%) of G1-12Far. G1-12Far was confirmed by NMR, IR, MALDI-mass, and elemental analysis. It was confirmed that G1-12Far had high purity by GPC.

¹ H NMR (ppm, CDCl ₃ ): = 0.07 (s, 12H, SiMe (G0)), 0.25-0.68 (m, 16H, CH2 (G0)), 1.52-1.80 (m, 144H, CH ₃ (G1) ), 1.88-2.20 (m, 96H, CH ₂ (G1)), 4.23-4.38 (m, 16H, OCH ₂ (G1)), 5.02-5.20, 5.33-5.37 (m, 36H, = CH (G1)) .

Elemental analysis: C ₁₉₂ H ₃₂₈ O ₁₆ Si ₈ (Mw = 3,112): C, 74.03%, H, 10.53%. Found: C, 73.92%, H, 10.41%. FT-IR (KBr, cm ⁻¹ ): υ _{(c = c)} 1667.

GPC: M _w / M _n = 1.01 (11499/11293), R _t = 16.40 min.

(Example 2)

(Molecular)

The above formula is a dendrimer with farnesyl functional groups, which has a siloxane tetramer in the center, grows siloxane functional groups up to 2 generations by allyloxy functional groups, and then adds 12 new SiCl ₃ functional groups by hydrosylation of the double bonds of the terminal groups, and farnesol The above compound was synthesized by the reaction with the functional dendrimer and the actual synthesis method is as follows.

63g of G2P-36Cl was dissolved by adding 225g of farnesol and 115g of TMEDA to toluene (2.5ℓ). The other synthesis and confirmation methods were the same as the synthesis and confirmation method of G1-12Far and 195g (87% ) G2-36Far.

¹ H NMR (ppm, CDCl ₃ ): = 0.06 (s, 12H, SiMe (G0)), 0.45-0.53 (m, 16H, CH ₂ (G0)), 1.42-1.85 (m, 432H, CH ₃ (G2) )), 1.85-2.21 (m, 288H, CH ₂ (G2)), 3.60-3.80 (m, 24H, OCH ₂ (G1)), 4.18-4.41 (m, 72H, OCH ₂ (G2)), 5.00- 5.20, 5.28-5.45 (m, 108H, = CH (G2)).

Elemental analysis: C ₅₈₈ H ₁₀₀₀ O ₅₂ Si ₂₀ (Mw = 9,448): C, 74.68%, H, 10.58%. Found: C, 74.33%, H, 10.28%. FT-IR (KBr, cm ⁻¹ ): υ _{(c = c)} 1667.

GPC: M _w / M _n = 1.03 (15996/15479), R _t = 15.62 min.

(Example 3)

(Molecular)

The above formula is a dendrimer with farnesyl functional group, which has siloxane tetramer in the center, grows siloxane tetrafunctional group to 3rd generation by allyloxy functional group, and adds 36 new SiCl ₃ functional groups by hydrosylation method of double bond of end group The above compound was synthesized by the reaction with the functional dendrimer and the actual synthesis method is as follows.

260 g of farnesol and 150 g of TMEDA were dissolved in toluene (2.5 L) and added to 71 g of G3P-108Cl. Other synthesis and identification procedures were the same as the synthesis and identification of G1-12Far. ) G3-108Far.

¹ H NMR (ppm, CDCl ₃ ): = 0.07 (s, 12H, SiMe (G0)), 0.45-0.71 (m, 16H, CH ₂ (G0)), 1.46-1.83 (m, 1296H, CH ₃ (G3 )), 1.83-2.20 (m, 864H, CH ₂ (G3)), 3.54-3,75 (m, 96H, OCH ₂ , (G1-G2)), 4.15-4.39 (m, 216H, OCH ₂ , ( G3)), 5.00-5.19, 5.28-5.44 (m, 324H, = CH (G3)). Elemental _{analysis: C 1776 H 3016 O 160 Si} 56 (Mw = 28,456): C, 74.89%, H, 10.59%. Found: C, 73.58%, H, 9.79%. FT-IR (KBr, cm ⁻¹ ): υ _{(c = c)} 1667.

GPC: M _w / M _n = 1.02 (21156/20570), R _t = 14.87 min.

(Example 4)

(Molecular)

The above formula is a dendrimer with farnesyl functional groups, which has a siloxane tetramer in the center, grows siloxane tetrafunctional groups to 4th generation by allyloxy functional groups, and then adds 108 new SiCl ₃ functional groups by hydrosylation of the double bonds of terminal groups, and farnesol The above compound was synthesized by the reaction with the functional dendrimer and the actual synthesis method is as follows.

99g of G4P-324Cl was dissolved in 334g of farnesol and 175g of TMEDA in toluene (3ℓ). Other synthesis and identification methods were carried out in the same manner as in the synthesis and identification of G1-12Far. 259g (61%) G4-324Far was obtained.

¹ H NMR (ppm, CDCl ₃ ): 0.06 (s, 12H, SiMe (G0)), 0,45-0.70 (m, 16H, CH ₂ (G0)), 1.38-1.79 (m, 3888H, CH ₃ (G4)), 1.79-2.30 (m, 2592H, CH ₂ (G4)), 3.52-3.75 (m, 312H, OCH ₂ (G1-G3)), 4.12-4.39 (m, 648H, OCH ₂ (G4) )), 4.95-5.21, 5.21-5.45 (m, 972H, = CH (G4)). Elemental analysis: C ₅₃₄₀ H ₉₀₆₄ O ₄₈₄ Si ₁₆₄ (Mw = 85,480): C, 74.96%, H, 10.60%. Found: C, 74.42%, H, 9.98%. FT-IR (KBr, cm ⁻¹ ): υ _{(c = c)} 1663.

GPC: M _w / M _n = 1.08 (32660/29970), R _t = 14.40 min.

(Example 5)

(Molecular)

Synthesis of G1n-1Far;

The chemical formula was obtained by synthesizing dimethylvinylchlorosilane and Si-H functional group of siloxane as a siloxane polymer having farnesyl functional groups by adding farnesol to the Si-Cl functional group.

To a solution of 93g G1P-1Cl in 2.5L of toluene, 169g (7.60 mmol) of farnesol and a solution of 500ml of TMED in 2.5L of toluene were added dropwise and stirred at room temperature for 1 hour.

After heating to 50 ° C. for 2 hours to confirm the completion of the reaction by ¹ H-NMR, the salt produced during the reaction was filtered off with pentane and the solvent was removed by distillation under reduced pressure. Farnesol and TMED added in excess during the reaction were removed by column chromatography using toluene and silica-gel, and the solvent was removed by distillation under reduced pressure to obtain 117 g (59%) of a colorless transparent gel, G1n-1Far.

Identification: Colorless transparent gelled compound, Mw ((C20H38O2Si2) n); 351.62, yield 1.17 g (3.33 mmol, 59%). 1 H-NMR (ppm, CDCl 3): = 0.08 (s, 9H, SiMe (G0, G1)), 0.35-0.65 (m, 4H, CH2 (G0)), 1.48-1.82 (m, 12H, CH3 (Far) ), 1.82-2.20 (m, 8H, CH2 (Far)), 4.08-4.20 (m, 2H, OCH2 (Far)), 5.05-5.20 (m, 3H, C = C (Far)), 5.25-5.50 ( m, 3H, C = C (Far)).

Synthesis of G1n-2Far;

The synthesis of G1n-2Far was synthesized by the same method as the synthesis of G1n-1Far, but the dehydrogenation reaction of siloxane polymer was obtained by adding farnesol to siloxane matrix containing two Si-Cl bonds with methyldichlorosilane. As follows.

To a solution of 35g of G1P-2Cl in 2L of toluene, a solution of 122g (5.49 mmol) of farnesol and 300ml of TMED in 2L of toluene was added dropwise and stirred at room temperature for 1 hour.

After heating to 50 ° C. for 2 hours to confirm the completion of the reaction by ¹ H-NMR, the salt produced during the reaction was filtered off with pentane and the solvent was removed by distillation under reduced pressure.

Farnesol and TMED added in excess during the reaction were removed by column chromatography using toluene and silica-gel, and solvent was removed by distillation under reduced pressure to obtain 60g (61%) of G1n-2Far as a colorless transparent gel.

Found: Colorless and transparent gelled compound, Mw ((C34 H60O3Si2) n); Yield 0.60 g (61%). 1 H-NMR (ppm, CDCl 3): = 0.09 (s, 6H, SiMe (G0, G1)), 0.38-0.70 (m, 4H, CH2 (G0)), 1.40-1.85 (m, 24H, CH3 (Far) ), 1.85 ~ 2.25 (m, 16H, CH2 (Far)), 4.10 ~ 4.33 (m, 4H, OCH2 (Far)), 5.00 ~ 5.22 (m, 6H, C = C (Far)), 5.22 ~ 5.42 ( m, 6H, C = C (Far)).

Synthesis of G1n-3Far;

The synthesis of G1n-2Far was synthesized by the same method as the synthesis of G1n-1Far, but the dehydrogenation reaction of siloxane polymer was obtained by adding farnesol to siloxane matrix containing three Si-Sl bonds with methyldichlorosilane. Same as

To a solution of 39 g of G1P-3Cl in 2 liters of toluene, 155 g (697 mmol) of farnesol and 250 ml of TMED in 1 liter of toluene were added dropwise and stirred at room temperature for 1 hour.

After heating to 50 ° C. for 2 hours to confirm the completion of the reaction by ¹ H-NMR, the salt produced during the reaction was filtered off with Pentane, and the solvent was removed by distillation under reduced pressure.

Farnesol and TMED added in excess during the reaction were removed by column chromatography using toluene and silica-gel, and solvent was removed by distillation under reduced pressure to obtain 94g (69%) of G1n-3Far as a colorless transparent gel.

Found: Colorless and transparent gelled compound, Mw ((C48 H82O4Si2) n); Yield 0.94 g (69%). 1 H-NMR (ppm, CDCl 3): = 0.08 (s, 3H, SiMe (G0)), 0.48-0.75 (m, 4H, CH 2 (G0)), 1.45-1.82 (m, 36H, CH 3 (Far)), 1.82 ~ 2.20 (m, 24H, CH2 (Far)), 4.20 ~ 4.40 (m, 6H, OCH2 (Far)), 5.00 ~ 5.20 (m, 9H, C = C (Far)), 5.20 ~ 5.40 (m, 9H, C = C (Far))

(Example 6)

(Molecular)

Synthesis of G2n-3Far;

The above formula is a siloxane dendrimer having farnesyl functional group, which is synthesized by dehydrogenation of Si-H functional group and dimethylvinylchlorosilane in siloxane, and then added to the Si-Cl functional group by adding HMe2SiCl incorporating allylalcohol. It was obtained by adding farnesol to the second generation parent dendrimer and the actual synthesis method is as follows.

A solution of 0.78 g (3.51 mmol) of farnesol and 250 ml of TMED in 1 L of toluene was added dropwise to a solution of 54 g of G2P-3Cl in 2 L of toluene, followed by stirring at room temperature for 1 hour.

After heating to 50 ° C. for 2 hours to confirm the completion of the reaction by ¹ H-NMR, the salt produced during the reaction was filtered off with pentane and the solvent was removed by distillation under reduced pressure.

Farnesol and TMED added in excess during the reaction were removed by column chromatography using toluene and silica-gel, and the solvent was removed by distillation under reduced pressure to obtain 56 g (52%) of a colorless transparent gel of G2n-3Far.

Found: Colorless transparent gelled compound, Mw ((C63 H118O7Si5) n); Yield 0.56 g (52%). 1 H-NMR (ppm, CDCl 3): = 0.09 (s, 21H, SiMe (G0, G2)), 0.40-0.72 (m, 16H, CH2 (G0, G1)), 1.40-1.90 (m, 36H, CH3 ( Far)), 1.90-2.20 (m, 24H, CH2 (Far)), 3.52-3.80 (m, 6H, OCH2 (G1)), 4.08-4.20 (m, 6H, OCH2 (Far)), 5.00-5.20 ( m, 9H, C = C (Far)), 5.20 ~ 5.40 (m, 9H, C = C (Far))

Synthesis of G2n-6Far;

The synthesis of G2n-6Far was synthesized by the same method as the synthesis of G2n-3Far, but the dehydrogenation reaction of siloxane dendrimer was obtained by adding farnesol to dendrimer matrix containing 6 Si-Cl bonds with methyldichlorosilane. Same as

In a solution of 63 g of G2P-6Cl in 2 liters of toluene, 172 g (773 mmol) of farnesol and 250 ml of TMED in 1 liter of toluene were added dropwise, followed by stirring at room temperature for 1 hour.

After heating to 50 ° C. for 2 hours to confirm the completion of the reaction by ¹ H-NMR, the salt produced during the reaction was filtered off with Pentane, and the solvent was removed by distillation under reduced pressure.

Farnesol and TMED added in excess during the reaction were removed by column chromatography using toluene and silica-gel, and the solvent was removed by distillation under reduced pressure to obtain 113 g (65%) of a colorless transparent gel of G2n-6Far.

Found: Colorless transparent gelled compound, Mw ((C105 H184O10Si5) n); Yield 1.13 g (65%). 1 H-NMR (ppm, CDCl 3): = 0.10 (s, 12H, SiMe (G0, G2)), 0.45-0.75 (m, 16H, CH2 (G0, G1)), 1.40-1.85 (m, 72H, CH3 ( Far)), 1.85-2.20 (m, 48H, CH2 (Far)), 3.60-3.80 (m, 6H, OCH2 (G1)), 4.10-4.40 (m, 12H, OCH2 (Far)), 5.00-5.20 ( m, 18H, C = C (Far)), 5.20 ~ 5.40 (m, 18H, C = C (Far))

Synthesis of G2n-9Far;

The synthesis of G2n-9Far was synthesized by the same method as the synthesis of G2n-6Far, but the dehydrogenation reaction of siloxane dendrimer and trichlorosilane was carried out by the addition of farnesol to dendrimer matrix having 9 Si-Cl bonds. As follows.

173g (7.78 mmol) of farnesol and 200ml of TMED in 1L of toluene were added dropwise to 46 g of G2P-9Cl in 2L of toluene, followed by stirring at room temperature for 1 hour.

After heating to 50 ° C. for 2 hours to confirm the completion of the reaction by ¹ H-NMR, the salt produced during the reaction was filtered off with Pentane, and the solvent was removed by distillation under reduced pressure.

Farnesol and TMED added in excess during the reaction were removed by column chromatography using toluene and silicagel, and solvent was removed by distillation under reduced pressure to obtain 120g (77%) of G2n-9Far as a colorless transparent gel.

Identification: Colorless transparent gelled compound, Mw ((C147 H250O13Si5) n); Yield 120 g (77%). 1 H-NMR (ppm, CDCl 3): = 0.07 (s, 3H, SiMe (G0)), 0.45 to 0.70 (m, 16H, CH 2 (G0, G1)), 1.40 to 1.80 (m, 108H, CH 3 (Far) ), 1.80-2.20 (m, 72H, CH2 (Far)), 3.55-3.80 (m, 6H, OCH2 (G1)), 4.10-4.40 (m, 18H, OCH2 (Far)), 4.95-5.20 (m, 27H, C = C (Far)), 5.20 ~ 5.40 (m, 27H, C = C (Far))

Spherical dendrimers (G1-G4) and rod dendrimers (A-F) containing farnesyl functional groups synthesized by the present invention and compounds produced by a series of chemical processes associated therewith are more functional than dendrimers produced by conventional manufacturing methods. It is a new synthesis method of next-generation dendrimer, which includes many functionalities in the low generation.

In particular, the present invention is a linear dendrimer containing a farnesyl functional group is a high molecular material having an effective structure when the effect of the dendrimer is not required precise molecular weight and this new compound will greatly contribute to the farnesol reactivity study.

1 is a schematic diagram of the skeleton structure of farnesol (farnesol) to be the material of the present invention

2 is the first to fourth generation compound and siloxane polymer synthesized in the present invention and

       Schematic diagram of the process of adding farnesol from the parent dendrimer applied to the siloxane dendrimer

3 is a 1H NMR spectrum for identifying first generation (G1-12Far), second generation (G2-36Far), third generation (G3-108Far), and fourth generation (G4-324Far).

Claims (10)

Dendrimer with farnesyl functional group, which has siloxane tetramer in the center and adds 4 new SiCl ₃ functional groups by hydrosylation of double bond among end groups of siloxane functional group, In the reaction with farnesol and the functional dendrimer, 65 g of G1P-12Cl dissolved 238 g of farnesol and 115 g of TMEDA in 2.5 L of toluene, and then slowly added and stirred for 2 hours to add HCl-TMEDA salt produced in the reaction process by adding pentane. After removal by filtration, all solvents and TMEDA added by distillation under reduced pressure were removed, and the remaining farnesol and TMEDA were removed by column-chromatography using silica-gel and toluene, followed by removal of the solvent by distillation under reduced pressure. Farnesyl dendrimer composite, characterized in that -12 Far (first generation). It is a dendrimer with farnesyl function, has siloxane tetramer in the center, grows siloxane acid group to second generation by allyloxy function, and adds 12 new SiCl ₃ functional groups by hydrosylation method of double bond of end group. In the reaction with farnesol and the functional dendrimer, 63 g of G2P-36Cl dissolved 225 g of farnesol and 115 g of TMEDA in 2.5 L of toluene, and slowly added, followed by stirring for 2 hours. HCl-TMEDA salt formed in the reaction process was added with pentane. After removal by filtration, all solvents and TMEDA added by distillation under reduced pressure were removed, and the remaining farnesol and TMEDA were removed by column-chromatography using silica-gel and toluene, followed by removal of the solvent by distillation under reduced pressure. Farnesyl dendrimer composite, characterized in that -36 Far (2nd generation). Dendrimer with farnesyl functional group, which has siloxane tetramer in the center, grows siloxane acid functional group to second generation by allyloxy functional group, and adds 36 new SiCl ₃ functional groups by double bond of end group by hydrosylation method, In the reaction with farnesol and the functional dendrimer, 71 g of G3P-108Cl was dissolved in 260 g of farnesol and 150 g of TMEDA in 2.5 L of toluene, and then slowly added. The mixture was stirred for 2 hours, followed by adding pentane to the HCl-TMEDA salt formed in the reaction process. After removal by filtration, all solvents and TMEDA added by distillation under reduced pressure were removed, and the remaining farnesol and TMEDA were removed by column-chromatography using silica-gel and toluene, followed by removal of the solvent by distillation under reduced pressure. Farnesyl dendrimer composite, characterized in that -108 Far (third generation). Dendrimer with farnesyl functional group, which has siloxane tetramer in the center, grows siloxane acid functional group to 3 generations by allyloxy functional group, and then adds 108 new SiCl ₃ functional groups by hydrosylation method of double bond of terminal group, In the reaction with farnesol and the functional dendrimer, 334 g of farnesol and 175 g of TMEDA were dissolved in 3 l of toluene and slowly added to the mixture, followed by stirring for 2 hours. HCl-TMEDA salt formed during the reaction was filtered by adding pentane. Dendrimer G4- obtained by removing all solvent and TMEDA added by distillation under reduced pressure, remaining farnesol and TMEDA by column-chromatography using silica-gel and toluene, and then removing the solvent by distillation under reduced pressure. Farnesyl dendrimer composite, characterized in that the 324 Far (4th generation). A siloxane polymer with farnesyl functional group, synthesized by dehydrogenation of Si-H functional group and dimethylvinylchlorosilane in siloxane, and then added 169 g (7.60) of 93g G1P-1Cl obtained by adding farnesol to Si-Cl functional group in 2.5L of toluene. mmol) farnesol and a solution of 500 ml TMED dissolved in 2.5 l of toluene was added dropwise, and the panesyl dendrimer composite obtained by stirring at room temperature for 1 hour. As a siloxane polymer having farnesyl functional group, 35g G1P-2Cl obtained by synthesizing dimethylvinylchlorosilane and Si-H functional group of siloxane by dehydrogenation reaction and then adding farnesol to Si-Cl functional group was dissolved in 122L (5.49 mmol) in a solution of toluene. Farnesol and 300 ml of TMED dissolved in toluene 2L solution was added dropwise and the farnesyl dendrimer composite obtained by stirring at room temperature for 1 hour. A siloxane polymer having farnesyl functional groups, which was synthesized by dehydrogenation of Si-H functional group and dimethylvinylchlorosilane of siloxane, and then 155 g (697) of 39 g of G1P-3Cl obtained by adding farnesol to Si-Cl functional group in 2 L of toluene. mmol) farnesol and 250 ml of TMED was added dropwise to a solution of toluene dropwise to the panesyl dendrimer composite, characterized in that obtained by stirring for 1 hour at room temperature. A siloxane polymer having farnesyl functional groups, which was synthesized by dehydrogenation of Si-H functional group and dimethylvinylchlorosilane in siloxane, and then added 54g of G2P-3Cl obtained by adding farnesol to Si-Cl functional group in 78L (351) of toluene. mmol) farnesol and 250 ml of TMED dissolved in 1 liter of toluene was added dropwise and stirred for 1 hour at room temperature, and the panesyl dendrimer composite obtained by heating to 50 ℃ for 2 hours. A siloxane polymer having farnesyl functional group, which is synthesized by dehydrogenation of Si-H functional group and dimethylvinylchlorosilane of siloxane, and then 172 g (773 g) of G2P-6Cl obtained by adding farnesol to Si-Cl functional group in 2 L of toluene. mmol) farnesol and 250 ml of TMED dissolved in 1 liter of toluene was added dropwise and then stirred for 1 hour at room temperature and warmed to 50 ℃ for 2 hours, farnesyl dendrimer composite. A siloxane polymer having farnesyl functional group, synthesized by dehydrogenation of Si-H functional group and dimethylvinylchlorosilane of siloxane, and then 173 g (778 g) of 46 g of G2P-9Cl obtained by adding farnesol to Si-Cl functional group in 2 L of toluene. mmol) farnesol and a solution of 200ml TMED dissolved in 1 liter of toluene was added dropwise and then stirred for 1 hour at room temperature and warmed to 50 ℃ for 2 hours, farnesyl dendrimer composite.