1,3-Dimethyl-tetrakis(2-triphenylsilylethyl)dimethyldisiloxane: a new carbosilane for the preparation of high-refractive-index films

Sacha Legrand; Ari Kärkkäinen

doi:10.1515/znb-2021-0046

Abstract

A new carbosilane has been synthesised in one step by hydrosilylation of 1,3-dimethyl-tetravinyldisiloxane with triphenyl silane. The new carbosilane has been characterized by 1D and 2D NMR, MS, and Gel Permeation Chromatography (GPC). The new carbosilane has been spin-coated on silicon wafers to prepare a film with very high refractive index (μ = 1.520) and excellent hydrophobicity. The film has also been analysed by Diffuse Reflectance Infrared Spectroscopy (DRIFT). The preparation of the new carbosilane does not generate waste, and its application can be easily scaled-up. Consequently, the new precursor is likely to be very useful for industrial optoelectronic applications.

Keywords: carbosilane; coating; high refractive index; hydrosilylation; spectroscopy

1 Introduction

A plethora of polycarbosilanes, compounds containing carbon-to-silicon (C–Si) covalent bonds, and related structures have been reported in the literature since the 1980s [1], [2], [3]. These macromolecules with excellent backbone variability [4] can be prepared following different synthetic strategies from a wide range of precursors. Wurtz-type condensation of bis(chlorosilyl) compounds, condensation of dichlorosilanes, transition metal-catalyzed C–C, and C–Si coupling, Si–Si bond-forming polymerization, ring opening polymerization of strained organosilacycles, electrochemical polymerization [5], hydrosilylation of dyines [6], reaction of (Me₃SiCH₂)SiHCl₂ and (Me₃SiCH₂)SiCl₃ with alkali metals constitute the main chemical platform employed for the synthesis of polycarbosilanes [7]. Silicon-carbon cyclic monomers are also important precursors used in the manufacturing of carbosilane macromolecules [8].

More advanced polycarbosilanes, such as hyperbranched polycarbosilanes have also been prepared using for example nucleophilic substitution reactions [9] or hydrosilylation polymerization [10]. Other relevant examples of organized carbosilane macromolecules include cyclolinear polycarbosilanes (CLPCS) containing the 1,3-disilacyclobutane (DSCB) ring bridged by various linking groups. CLPCSs have been synthesized by acyclic diene metathesis polymerization (ADMET) [11] and Grignard coupling reactions [12]. Additionally, ADMET polymerization in combination with nucleophilic substitution are useful methods for the preparation of other functionalized carbosilane polymers [13]. Thus, in 2014 Makarova et al. [14] demonstrated that heterofunctional polycondensation and polyaddition of difunctional organocyclosiloxanes and organocyclocarbosiloxanes yielded self-organized cyclolinear organocarbosiloxane polymers. Additionally, according to Mukbaniani and co-workers, organosilicon copolymers with carbocyclosiloxane fragments in the dimethylsiloxane backbone can be synthesized using hydride polyaddition reaction [15]. Hyperbranched ferrocene-containing poly(boro)carbosilanes having low Mark–Houwink–Sakurada exponents have been prepared using a convenient A ₂ + B ₃ approach [16]. The topological analysis of soluble A ₂ + B ₃ type polycarbosilanes has been carried out using the terminal index (TI) [17].

Polycarbosilanes have been found to be very useful in a wide range of applications, as e.g., in chemical sensors [18, 19], for manufacturing SiC fibers [20] and ceramic materials [21, 22], and for the formation of thermotropic mesophases [23]. Specific polycarbosilanes containing the Si–CH₂–Si bridging groups in their backbone are valuable synthetic building blocks for the construction of functional polymeric materials [24]. It has also been demonstrated that hyperbranched polycarbosilanes can be used in catalysis, host-guest chemistry and liquid crystals preparation [25]. Carbosilane π-conjugated-type copolymers, synthesized using the Heck coupling, can be employed for electroluminescence device (ELD) applications [26]. Polycarbosilanes are also precursors for silicon carbide materials [27], and ceramic composites for aerospace techniques and associated applications [28]. Carbosilane polymers, functionalized with hexafluoro-2-propanol (HFIP), have been used for chemical pre-concentrator applications [29]. Crosslinked polycarbosilanes, applied as interlayer dielectric materials for advanced interconnect technology [30], and siloxane–silsesquioxane hybrid thin films for large-scale-integration interlayer dielectrics with excellent mechanical properties and low dielectric constants [31], are other relevant examples. Finally, theoretical studies on carbosilane oligomers, have also been reported in the literature [32].

Dendritic carbosilanes have been described extensively and excellent reviews have been written by several research groups [33], [34], [35]. A notable review regarding the preparation and properties of heteroatom-containing dendritic polycarbosilanes has been published by Majoral and Caminade [36]. Carbosilane dendrimers with perfluorinated end groups are also well-known [37], and it has been demonstrated that carbosilane dendrimers functionalized with iminopyridine ligands are very valuable chelating agents for Pd-based catalytic reactions [38]. Dendritic polycarbosilanes have also been employed to form macro-crystalline ordered phases [39].

However, despite the overabundance of polycarbosilanes and dendritic carbosilanes reported in the literature, only a limited number of carbosilanes has been used for the development of high-refractive-index (HRI) materials. These materials are currently very important, since they are required for a wide range of optoelectronic applications, including anti-reflecting coatings [40], displays and optoelectronic devices [41], complementary metal oxide semiconductor image sensors, and micro lens components for charge coupled devices [42].

One of the rare successful examples of HRI polycarbosilanes are poly(silylenevinylenes), having refractive indices as high as 1.718, high modified Abbe numbers and low optical dispersion [43]. In a noteworthy study by Kudo et al. [44], polycarbosilanes with high refractive index (up to 1.711) were prepared by A ₂ + B _n (n = 2, 3 and 4)-type hydrosilylation reactions. Thiol-ene coupling reactions of tetravinyl monomers have also been employed for the formation of highly cross-linked prepolymer gels exhibited high refractive indices ranging from 1.590 to 1.703, and Abbe numbers between 24.3 and 45.0 [45]. Unfortunately, the manufacturing procedures described above can be very laborious, require complex synthetic strategies, use expensive starting materials, and are very difficult to scale-up. Therefore, they are not suitable for industrial purposes. Consequently, there is a strong need to design, prepare and develop carbosilanes, which can be used as high-refractive-index materials for commercial applications. In this perspective, and considering the environmental impact, the present work aims to develop a new high-refractive-index carbosilane, which can be applied for the preparation of highly valuable optoelectronic materials.

2 Results and discussion

We have prepared a new high-refractive-index carbosilane using 1,1,3,3-tetravinyldimethyldisiloxane (1) as the core molecule and triphenylsilane (2) as the second reactant. It has been previously demonstrated that phenyl and aromatic rings are suitable chemical moieties used for the manufacturing of polymers with high-refractive-index value [46], [47], [48]. Catalytic hydrosilylation using the Speier catalyst (H₂PtCl₆·H₂O) at T = 70 °C between the vinyl groups present in 1 and the Si–H moiety present in 2 gave 1,3-dimethyl-tetrakis(triphenylsilylethyl)disiloxane (3) in quantitative yield (Scheme 1).

Scheme 1:

Reaction condition: (i) H₂PtCl₆·H₂O (0.1 mL, 10% in 2-propanol), T = 60–70 °C.

The compound 3 was fully characterized by 1D and 2D NMR, and MS spectroscopies. In the ¹H and ¹³C NMR spectra of 3 (Figures S1 and S2, respectively; Supplementary material available online), no signals arising from remaining vinyl groups were observed, which confirms the completion of the hydrosilylation reaction. Additionally, new signals corresponding to the synthesized Si(CH₂)₂Si bridges present in 3 are observed at δ = 1.24–1.08 and 0.63 ppm in the ¹H NMR spectrum, and at δ = 8.96 and 5.16 ppm in the ¹³C NMR spectrum. The hydrosylilation obviously proceeded through an anti-Markovnikov mechanism [49, 50]. The assignments of the peaks present in the ¹H and ¹³C NMR spectra were confirmed with the help of ¹H–¹³C heteronuclear single quantum correlation (HSQC) experiments. The HSQC spectrum of 3 is shown in Figure 1. Correlation points were noticed between the proton b and the carbon atom at δ = 8.96 ppm, and the proton c and the carbon atom at δ = 5.16 ppm, respectively. An expansion of the HSQC spectrum is shown in Figure S3 (Supplementary material).

Figure 1:

HSQC spectrum of the carbosilane 3 in acetone-d ₆.

Moreover, an LC-MS experiment was used to further characterize the target compound 3. A peak with M = 1273 g mol⁻¹ was noticed in the LC-MS chromatogram (Figure S4; Supplementary material), which corresponds to the molecular weight of 3 with a sodium as a cation. A detailed expansion of the LC-MS chromatogram is shown in Figure S5 (Supplementary material).

Compound 3 was further characterized using GPC (gel permeation chromatography). The GPC chromatogram of 3 is shown in Figure 2. The molecular weights and the polydispersity index (PDI) of 3 are presented in Table 1. Importantly, the PDI value is very close to 1, which indicates that the carbosilane 3 is monodisperse. Thus, no oligomers or polymers have been formed during the hydrosilylation process.

Figure 2:

GPC chromatogram of the carbosilane 3 (M_n = 786 g mol^–1, M_w = 802 g mol^–1 and MP = 858 g mol^–1).

Table 1:

Number-average molecular weight (M _n), weight-average molecular weight (M _w), molecular weight of the highest peak (MP), higher-average molecular weights (M _z and M _z + 1) and polydispersion index (PDI) of the carbosilane 3.

M _n (g mol⁻¹)	M _w (g mol⁻¹)	MP	M _z (g mol⁻¹)	M _z + 1 (g mol⁻¹)	PDI
786	802	858	816	829	1.0195

The higher-average molecular weights (M _w, M _z and M _z + 1) are calculated as follows: M = (Σ N _i M _i ⁿ⁺¹)/(ΣN _i M _i ⁿ) where n=1 gives M = M _w, n=2 gives M = M _z, n=3 gives (M = M _z + 1) and N _i = number of chains in fractions i, M _i = molecular weight of chains in fraction i.

All together, these experiments allowed us to confirm the successful preparation of the carbosilane 3 by hydrosilylation reaction between 1,1,3,3-tetravinyldimethyldisiloxane (1) and triphenylsilane (2) using the Speier catalyst (H₂PtCl₆·H₂O).

The refractive index of the carbosilane 3 was determined in toluene solution. The refractive index values at different concentrations are presented in Figure 3. The refractive indices of 3 are higher compared to toluene (1.497) and varied from 1.503 (lower concentration) to 1.520 (higher concentration). This observation also corroborates our previous results claiming that many phenyl rings present in a polymer backbone significantly increase the refractive index of the final material [46], [47], [48].

$Figure 3: Refractive index μ of the carbosilane 3 at different concentrations in toluene.$

Figure 3:

Refractive index μ of the carbosilane 3 at different concentrations in toluene.

The performance of the carbosilane 3 as a coating material for the preparation of a high-refractive-index film was also investigated. The carbosilane 3 was first dissolved in toluene (c = 3.65 g mol⁻¹). Then, the solution was spread on a silicon wafer by using the spin-coating technique at 400 rpm min⁻¹ for 7 s and then at 1000 rpm min⁻¹ for 20 s. The resulting film was baked for 2 h at T = 120 °C and then for 75 min at T = 150 °C. After cooling to room temperature and visual inspection, the thickness and refractive index of the film were measured using an ellipsometer. The thickness and the refractive index of the film were found to be 1135 nm and 1.51 (Table 2), respectively. Moreover, the surface wettability of the prepared film was assessed by the sessile drop method. The water contact angle of the coated silicon wafer was found to be 101.35° (Table 2), which is significantly higher in comparison to similar uncoated silicon wafers, which have a contact angle of about 33.51°. The increase of surface hydrophobicity observed for the film is due to the presence of the hydrophobic phenyl rings present in the carbosilane 3.

Table 2:

Characteristics of the film made from the carbosiloxane 3.

Thickness (nm)	Refractive index	Contact angle (°)
1135	1.520	101.35

The film was analysed by Diffuse Reflectance Infrared Spectroscopy (DRIFT) and the spectrum is shown in Figure S6 (Supplementary material). The main characteristic bands in the spectrum of the silicon wafer coated with 3 are found for CH_aromatic and CH₂–CH₂ at 2871–3066 cm⁻¹, CH_aromatic at 1487 and 717 and 688 cm⁻¹, Si–CH₃ at 1247 cm⁻¹, Si-Ph at 1186 cm⁻¹, Si–O–Si at 1028 cm⁻¹, and Si–CH₂–CH₂ at 900 cm⁻¹, which correspond to the signals of the main chemical groups found in the carbosilane 3.

3 Conclusion

We report the design, synthesis, characterization, and preliminary optical studies of a new carbosilane. The carbosilane has been analyzed by 1D and 2D NMR spectroscopy and MS spectrometry and GPC. The refractive index of the new carbosilane in solution has been demonstrated to be as high as 1.520. The new carbosilane has also been used to prepare a coated silicon wafer with high refractive index, which was characterized by DRIFT spectroscopy and shown to be an excellent hydrophobic material. Consequently, such carbosilanes are expected to be very useful precursors for the preparation of organic materials with great potential for optical, and photonic applications. Importantly, the presented method is scalable for industrial applications, does not generate organic wastes, and as a result can be applied for manufacturing purposes.

4 Experimental section

The starting materials employed were purchased from commercial suppliers and were used without further purification.

4.1 Nuclear magnetic resonance (NMR), liquid chromatography – mass spectroscopy (LC-MS) and diffuse reflectance infrared spectroscopy (DRIFT)

NMR spectra were recorded on a Bruker Asend™ 400 spectrometer (400 MHz for ¹H and 100 MHz ¹³C). Acetone-d ₆ was used as a solvent, and the signal of the solvent served as internal standard. Chemical shifts were expressed in ppm, followed by their multiplicity (s, singlet; m, multiplet) and number of protons. The HSQC experiment was performed using a HSQCEDETGP pulse sequence, and a 1.5 s relaxation delay. The LC-MS experiments were performed with a Waters 2690 Alliance HPLC system (column: Waters Symmetry C18) coupled to an LCT TOF time-of-flight mass spectrometer with LockSpray ion source. The FT-IR spectrometer Invenio^® (Bruker) coupled to a DTSG (deuterated triglycine sulfate)-based detector, was used to perform the DRIFT experiments and to collect the signals of the film in the range from 400 to 4000 cm⁻¹.

4.2 Gel permeation chromatography (GPC)

The chromatographic system consisted of a GPC apparatus equipped with an isocratic HPLC pump and a refractive index detector. The carbosilane 3 (0.20 g, 0.16 mmol) was dissolved in THF (HPLC grade; 2.30 g, 31.89 mmol). The analyte injection volume was 100 µL, the flow rate was 0.70 mL min⁻¹, and the column temperature was set to 40 °C. Four polystyrene exclusion-based columns were used. The mobile phase was THF (HPLC grade). The weight-average molecular weight (M _w) of the polymers were determined using internal standards, e.g. two series of polystyrenes (Serie A: 5 polystyrenes with M _w = 120,000, 42,400, 10,700, 2640, 474 g mol⁻¹ and Serie B: 4 polymers with M _w = 193,000, 16,700, 6540, 890 g mol⁻¹).

4.3 Synthesis and characterization of 1,3-dimethyl-tetrakis(2-triphenylsilylethyl)disiloxane (3)

In a 250 mL round bottom flask, 1,3-dimethyl-tetravinyldisiloxane 1 (2 g, 9.5 mmol) was mixed with triphenylsilane 2 (9.90 g, 38.0 mmol). Then, the catalyst H₂PtCl₆·H₂O (0.1 mL, 10% in 2-propanol, 0.02 mmol) was added at T = 60 °C. The colour of the reaction mixture rapidly changed from slightly yellow to brown. The reaction mixture was then stirred at T = 70 °C for 1 h. The reaction mixture was then cooled to room temperature giving the compound 3 (11.87 g, 9.5 mmol, 100%) as a very viscous brown oil. – IR (film): ν = 3066–2871 (CH_ar and CH₂–CH₂: C–H bending and CH₂ stretching), 1487 (CH_ar: C–H bending), 1247 (Si–CH₃: CH₃ deformation), 1186 (Si–Ph: Si–C stretching), 1028 (Si–O–Si: Si–O–Si stretching), 900 (Si–CH₂–CH₂: CH₂ wag), 717 and 688 (both CH_ar: C–H wag) cm⁻¹. – ¹H NMR (400 MHz, acetone-d ₆, 20 °C): δ = 7.62–7.26 (m, 60H, H_ar), 1.24–1.08 (m, 8H, Ph₃SiCH₂CH₂), 0.62 (m, 8H, Ph₃SiCH₂CH₂), 0 (s, 6H, SiCH₃). – ¹³C NMR (100 MHz, acetone-d ₆, 20 °C): δ = 136.91, 136.46, 136.20, 135.77, 135.56, 130.17, 128.64 (all C_ar), 8.96 (Ph₃SiCH₂CH₂), 5.16 (Ph₃SiCH₂CH₂), −2.21 (SiCH₃). – LCMS: m/z = 1273 [M+Na]⁺.

4.4 Determination of the refractive index of liquid samples

The refractive indices of liquid samples have been determined using a RE40D refractometer from Mettler Todelo. The experiments were performed at 20 °C using de-ionized water as reference. The measurements were repeated 3 times and the average was considered. The order of experimental error is ±2%.

4.5 Preparation and curing of a film using compound (3) as coating material and silicon wafer as substrate

The carbosilane 3 was dissolved in toluene (c = 3.65 g mol⁻¹). The reaction mixture was then deposited using the spin-coating method, on a silicon wafer at 400 rpm min⁻¹ for 7 s, and 1000 rpm min⁻¹ for 20 s using a RCD8-spin coater instrument. The silicon wafer (diameter: 150 mm; thickness: 675 ± 25 μm; sensitivity: 1–30 Ω cm) was purchased from Si-Mat silicon materials. The resulting coated silicon wafer was then subjected to immediate curing at atmospheric environment in an oven at T = 120 °C for 2 h, and T = 150 °C for 75 min.

4.6 Film characterization

4.6.1 Thickness and refractive index

The film thickness and refractive index were measured at five distinct positions with ellipsometer AutoEl-IV equipped with a tungsten lamp. The order of experimental error for refractive index measurements is ±2%.

4.6.2 Contact angle

The surface wettability of the prepared film was assessed by sessile drop method. This experiment was performed by measuring the contact angle using Attention Theta Optical Tensiometer, equipped with a digital video camera. A drop of distilled water (4 µL) was deposited on the surface of the film with a micro-syringe. The angle between the drop and surface of the film on both sides was measured at room temperature. The mean values were calculated in three random droplets. Image recording settings were adjusted to 10.0 s at 20% (12 FPS) and the analysis mode was based on the Young–Laplace equation.

5 Supporting information

¹H and ¹³C NMR spectra, the ¹H-¹³C heteronuclear single quantum correlation (HSQC) spectrum with its expansion and the MALDI mass spectrum with its expansion of 1,3-dimethyl-tetrakis(2-triphenylsilylethyl)dimethyldisiloxane (3), and a DRIFT spectrum of a silicon wafer coated with compound 3 are given as supplementary material available online (https://doi.org/10.1515/znb-2021-0046).

Corresponding author: Sacha Legrand, Optitune Oy, Tutkijankuja 5, FIN-90590 Oulu, Finland, E-mail: sacha.legrand@optitune.com

Acknowledgments

We thank Päivi Joensuu (University of Oulu, Finland) for assistance with LC-MS measurements, Eero Hietala (VTT, Technical Research Center of Finland) for assistance with DRIFT measurements, Kaisa Malo for assistance with spin-coating experiments, and Paula Keski-Korsu-Piekkari for fruitful discussions (both from Optitune Oy).

Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: None declared.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Seyferth, D. ACS Symp. Ser. 1988, 360, 21–42; https://doi.org/10.1021/bk-1988-0360.ch003.Search in Google Scholar

2. Interrante, L. V., Shen, Q. Polycarbosilanes. In Silicon-Containing Polymers; Jones, R. G., Ando, W., Chojnowski, J., Eds. Springer: Dordrecht, 2000; pp. 247–321; https://doi.org/10.1007/978-94-011-3939-7_10.Search in Google Scholar

3. Matsumoto, K. Polycarbosilanes. In Encyclopedia of Polymer Science and Technology; Mark, H. F., Series Ed. John Wiley & Sons: Hoboken, N. J., 4th ed., Vol. 10, 2014; pp. 386–398.10.1002/0471440264.pst428Search in Google Scholar

4. Weber, W. P. Trends Polym. Sci. 1993, 1, 356–360; https://doi.org/10.1016/0968-0004(93)90076-y.Search in Google Scholar

5. Ohsita, J., Kunai, A. Acta Polym. 1998, 49, 379–403.10.1002/(SICI)1521-4044(199808)49:8<379::AID-APOL379>3.0.CO;2-ZSearch in Google Scholar

6. Sanchez, J. C., Trogler, W. C. Macromol. Chem. Phys. 2008, 209, 1527–1540; https://doi.org/10.1002/macp.200800235.Search in Google Scholar

7. Ouyang, G., Simons, R., Tessier, C. Polym. Mater. Sci. Eng. 1994, 71, 318.Search in Google Scholar

8. Finkelshtein, E. S., Ushakov, N. V., Gringolts, M. L. Polycarbosilanes based on silicon-carbon cyclic monomers. In Silicon Polymers. Advances in Polymer Science; Muzafarov, A., Ed. Springer: Berlin, Heidelberg, Vol. 235; 2010, pp. 111–159; https://doi.org/10.1007/12_2009_39.Search in Google Scholar

9. Interrante, L., Shen, Q. Hyperbranched polycarbosilanes via nucleophilic substitution reactions. In Silicon-Containing Dendritic Polymers; Dvornic, P. R., Owen, M. J., Eds.; Advances in Silicon Science, Matinsons, J., Series Ed. Springer: Dordrecht, Vol 2, 2009; pp. 315–343.10.1007/978-1-4020-8174-3_12Search in Google Scholar

10. Schüle, H., Frey, H. Hyperbranched polycarbosilanes and polycarbosiloxanes via hydrosilylation polymerization. In Silicon-Containing Dendritic Polymers; Dvornic, P. R., Owen, M. J., Eds.; Advances in Silicon Science. Matinsons, J., Series Ed. Springer: Dordrecht, Vol 2, 2009; pp. 345–375.10.1007/978-1-4020-8174-3_13Search in Google Scholar

11. Cummings, S., Smith, D., Wagener, K., Miller, R., Ginsburg, E. Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 1995, 36, 696–698.Search in Google Scholar

12. Interrante, L. V., Rathore, J. S. Dalton Trans. 2010, 39, 9193–9202; https://doi.org/10.1039/c0dt90065f.Search in Google Scholar

13. Church, A. C., Cameron, J. H., Wagener, K. B. Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2001, 42, 235.Search in Google Scholar

14. Makarova, N. N., Astapova, T. V., Buzin, A. I., Polishchuk, A. P., Chizhova, N. V., Petrova, I. M. Int. J. Mol. Sci. 2013, 14, 18215–18238; https://doi.org/10.3390/ijms140918215.Search in Google Scholar

15. Zaikov, G. E., Eds. Organosilicon Copolymers with Carbocyclosiloxane Fragments in Dimethylsiloxane Backbone; Nova Science Publishers, Inc.,: Hauppauge, N. Y. I. Javakhishvili Tbilisi Sate University, Tbilisi, Georgia.Search in Google Scholar

16. Kong, J., Schmalz, T., Motz, G., Müller, A. H. E. Macromolecules 2011, 44, 1280–1291; https://doi.org/10.1021/ma1029086.Search in Google Scholar

17. Chen, H., Kong, J. J. Phys. Chem. B 2014, 118, 3441–3450; https://doi.org/10.1021/jp411888p.Search in Google Scholar

18. Houser, E. J., Duane, D. L., Stepnowski, J. L., Papantonakis, M. R., Ross, S. K., Stepnowski, S. V., Snow, E. S., Perkins, K. F., Bryant, C., LaPuma, P., Hook, G., McGill, R. A. ACS Symp. Ser. 2007, 980, 71–87; https://doi.org/10.1021/bk-2007-0980.ch005.Search in Google Scholar

19. Grate, J. W., Kaganove, S. N., Nelson, D. A. Chem. Innovat. 2000, 30, 29–37.Search in Google Scholar

20. Ishikawa, T. New Mater. New Process. 1985, 3, 1–2.10.1002/ace.36719852803Search in Google Scholar

21. Greil, P., Emy, T., Suttor, D. Ceram. Trans. 1995, 51, 171–178.Search in Google Scholar

22. Birot, M., Pillot, J.-P., Dunogues, J. Chem. Rev. 1995, 95, 1443–1477; https://doi.org/10.1021/cr00037a014.Search in Google Scholar

23. Ganicz, T., Wlodzimierz, W. A. Prog. Polym. Sci. 2002, 28, 303–329.10.1016/S0079-6700(02)00020-5Search in Google Scholar

24. Interrante, L. V., Rushkin, I., Shen, O. Appl. Organomet. Chem. 1998, 12, 695–705; https://doi.org/10.1002/(sici)1099-0739(199810/11)12:10/11<695::aid-aoc774>3.0.co;2-7.10.1002/(SICI)1099-0739(199810/11)12:10/11<695::AID-AOC774>3.0.CO;2-7Search in Google Scholar

25. Schlenk, C., Frey, H. Monatsh. Chem. 1999, 130, 3–14; https://doi.org/10.1007/pl00010172.Search in Google Scholar

26. Kim, H. K., Baek, N. S., Paik, K. L., Lee, Y., Lee, J. H. ACS Symp. Ser. 2005, 888, 247–263.10.1021/bk-2005-0888.ch019Search in Google Scholar

27. Pillot, J. P., Birot, M., Duboudin, F., Bordeau, M., Biran, C., Dunogues, J. Front. Organosilicon Chem., Proc. Int. Symp. Organosilicon Chem., 9th, 1991; pp. 40–49.Search in Google Scholar

28. Solntsev, St. S. Russ. J. Gen. Chem. 2011, 81, 992–1000; https://doi.org/10.1134/s1070363211050306.Search in Google Scholar

29. Simonson, D. L., McGill, R. A., Higgins, B. A. Proc. SPIE 2008, 6945, 69451R/1–69452R/8.10.1117/12.781728Search in Google Scholar

30. Wang, P.-I., Wu, Z., Lu, T.-M., Interrante, L. V. J. Electrochem. Soc. 2006, 153, G267–G271; https://doi.org/10.1149/1.2167932.Search in Google Scholar

31. Yim, J.-H., Lyu, Y.-Y., Jeong, H.-D., Mah, S. K., Hyeon-Lee, J., Hahn, J.-H., Kim, G. S., Chang, S., Park, J.-G. J. Appl. Polym. Sci. 2003, 90, 626–634; https://doi.org/10.1002/app.12591.Search in Google Scholar

32. Liao, R., Liu, C., Sa, R., Wu, K. J. Mol. Struct. Theochem 2007, 823, 28–33; https://doi.org/10.1016/j.theochem.2007.08.027.Search in Google Scholar

33. Roovers, J., Ding, J. Carbosilane dendrimers. In Silicon-Containing Dendritic Polymers; Dvornic, P. R., Owen, M. J., Eds.; Advances in Silicon Science, Vol 2. Matinsons, J., Series Ed. Springer: Dordrecht, 2009; pp. 31–74.10.1007/978-1-4020-8174-3_3Search in Google Scholar

34. Lang, H., Luhmann, B. Adv. Mater. 2001, 13, 1523–1540; https://doi.org/10.1002/1521-4095(200110)13:20<1523::aid-adma1523>3.0.co;2-p.10.1002/1521-4095(200110)13:20<1523::AID-ADMA1523>3.0.CO;2-PSearch in Google Scholar

35. Son, D. Y. Chem. Commun. 2013, 49, 10209–10210; https://doi.org/10.1039/c3cc44067b.Search in Google Scholar

36. Majoral, J.-P., Caminade, A.-M. Chem. Rev. 1999, 99, 845–880; https://doi.org/10.1021/cr970414j.Search in Google Scholar

37. Stark, B., Lach, C., Frey, H., Stuhn, B. Macromol. Symp. 1999, 146, 33–39; https://doi.org/10.1002/masy.19991460107.Search in Google Scholar

38. Martinez-Olid, F., Benito, J. M., Flores, J. C., de Jesus, E. Isr. J. Chem. 2009, 49, 99–108; https://doi.org/10.1560/ijc.49.1.99.Search in Google Scholar

39. Roovers, J. Macromol. Symp. 1997, 121, 89–93; https://doi.org/10.1002/masy.19971210108.Search in Google Scholar

40. Krogman, K. C., Druffel, T., Sunkara, M. K. Nanotechnology 2005, 16, S338–S343; https://doi.org/10.1088/0957-4484/16/7/005.Search in Google Scholar PubMed

41. Nakaruma, T., Fujii, H., Juni, N., Tsutsumi, N. Opt. Rev. 2006, 13, 104–110.10.1007/s10043-006-0104-8Search in Google Scholar

42. Suwa, M., Niwa, H., Tomikawa, M. J. Photopolym. Sci. Technol. 2006, 19, 275–276; https://doi.org/10.2494/photopolymer.19.275.Search in Google Scholar

43. Lu, P., Lam, J. W. Y., Liu, J., Jim, C. K. W., Yuan, W., Chan, C. Y. K., Xie, N., Hu, Q., Cheuk, K. K. L., Tang, B. Z. Macromolecules 2011, 44, 5977–5986; https://doi.org/10.1021/ma201203w.Search in Google Scholar

44. Kudo, H., Fujiwara, Y., Miyasaka, M., Makoto, N., Nishikubo, T. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 5746–5751; https://doi.org/10.1002/pola.24379.Search in Google Scholar

45. Bhagat, S. D., Chatterjee, J., Chen, B., Stiegman, A. E. Macromolecules 2012, 45, 1174–1181; https://doi.org/10.1021/ma202467a.Search in Google Scholar

46. Legrand, S., Hannu-Kuure, M., Kärkkäinen, A. J. Appl. Polym. Sci. 2021, 138, 49877–49892; https://doi.org/10.1002/app.49877.Search in Google Scholar

47. Legrand, S., Hannu-Kuure, M., Kärkkäinen, A. Z. Naturforscher 2020, 75b, 359–363; https://doi.org/10.1515/znb-2019-0199.Search in Google Scholar

48. Legrand, S., Kärkkäinen, A. J. Appl. Polym. Sci. 2021, 138, 50467–50481; https://doi.org/10.1002/app.50467.Search in Google Scholar

49. Hofmann, R. J., Vlatkovic, M., Wiesbrock, F. Polymers 2017, 9, 534–571; https://doi.org/10.3390/polym9100534.Search in Google Scholar PubMed PubMed Central

50. Marciniec, B., Ed. Hydrosilylation, A comprehensive review on recent advances. In Advances in Silicon Science; Matinsons, J., Series Ed. Springer: Dordrecht, Vol. 1, 2009.10.1007/978-1-4020-8172-9Search in Google Scholar

Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2021-0046).

Received: 2021-03-29

Accepted: 2021-06-01

Published Online: 2021-07-09

Published in Print: 2021-08-26

Supplementary Material