Yttrium Complexes and Related Methods

Abstract

Yttrium complexes and related methods are provided. The method for preparing the yttrium complexes includes contacting a metal alkylcyclopentadienyl compound with a yttrium trihalide compound in a non-coordinating solvent to obtain a tris(alkylcyclopentadienyl)yttrium complex. The composition includes the tris(alkylcyclopentadienyl)yttrium complex.

Description

[Technical Field]

[0001] The present disclosure relates to yttrium complexes and related methods. [Background technology]

[0002] Conventional synthesis of yttrium complexes requires multiple steps, which results in low yield and low purity of the yttrium complexes. Summary of the Invention

[0003] Some embodiments relate to a composition. In some embodiments, the composition comprises a compound of the following formula: TIFF2026500860000002.tif79170[In the formula, R 1 and R 2 are each independently hydrogen or alkyl. and the complex comprises: 1 having a purity of at least 70% as determined by H NMR; This complex is a non-sublimation product.

[0004] Some embodiments relate to methods of forming a complex. In some embodiments, the methods include contacting a metal alkylcyclopentadienyl compound with a yttrium trihalide compound in a non-coordinating solvent to obtain a tris(alkylcyclopentadienyl)yttrium complex. In some embodiments, the methods include removing at least a portion of the non-coordinating solvent to obtain a solid-phase tris(alkylcyclopentadienyl)yttrium complex. In some embodiments, the methods include recrystallizing the tris(alkylcyclopentadienyl)yttrium complex.

[0005] Some embodiments of the present disclosure are described herein, by way of example only, with reference to the accompanying drawings. With specific reference now to the drawings in detail, it is emphasized that the illustrated embodiments are by way of example and for purposes of illustrative discussion of embodiments of the present disclosure. In this regard, the description taken together with the drawings will make apparent to those skilled in the art how embodiments of the present disclosure may be practiced. [Brief explanation of the drawings]

[0006] [Figure 1] 1 is a flowchart of a method for preparing an yttrium complex, according to some embodiments. DETAILED DESCRIPTION OF THE INVENTION

[0007] Among these disclosed benefits and improvements, other objects and advantages of the present disclosure will become apparent from the following description taken in conjunction with the accompanying drawings. While detailed embodiments of the present disclosure are disclosed herein, it should be understood that the disclosed embodiments are merely exemplary of the present disclosure, which may be embodied in various forms. Moreover, each of the examples shown for various embodiments of the present disclosure is intended to be illustrative and not limiting.

[0008] All prior patents and publications referenced herein are incorporated by reference in their entirety.

[0009] Throughout this specification and claims, the following terms have the meanings expressly associated therewith herein, unless the context clearly dictates otherwise. As used herein, the phrases "in one embodiment," "in an embodiment," and "in some embodiments" do not necessarily refer to the same embodiment, but may. Additionally, as used herein, the phrases "in another embodiment" and "in some other embodiments" do not necessarily refer to different embodiments, but may. It is intended that all embodiments of the present disclosure be combinable without departing from the scope or spirit of the disclosure.

[0010] As used herein, the term "based on" is not exclusive and allows for based on additional unrecited factors unless the context clearly dictates otherwise. Furthermore, throughout this specification, the meanings of "a," "an," and "the" include plural references. The meaning of "in" includes "in" and "on."

[0011] As used herein, the term "alkyl" refers to a hydrocarbon compound having 1 to 30 carbon atoms. An alkyl having n carbon atoms is defined as "C n For example, "C alkyl" may include n-propyl and isopropyl. Alkyl having a range of carbon atoms, such as 1 to 30 carbon atoms, may be specified as C1-C 30 In some embodiments, alkyl is linear. In some embodiments, alkyl is branched. In some embodiments, alkyl is substituted. In some embodiments, alkyl is unsubstituted. In some embodiments, alkyl is C1-C 10Alkyl, C1-C9 alkyl, C1-C8 alkyl, C1-C7 alkyl, C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, C1-C2 alkyl, C2-C 10 Alkyl, C3-C 10 Alkyl, C4-C 10 Alkyl, C5-C 10 Alkyl, C6-C 10 Alkyl, C7-C 10 Alkyl, C8-C 10 In some embodiments, alkyl includes at least one of C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, C9 alkyl, C 10 In some embodiments, the alkyl includes at least one of methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, isobutyl, sec-butyl, n-pentyl, 1,1-dimethylethyl (t-butyl), n-pentyl, isopentyl, n-hexyl, isohexyl, 3-methylhexyl, 2-methylhexyl, heptyl, octyl, nonyl, decyl, dodecyl, octadecyl, or any combination thereof. In some embodiments, the alkyl does not include C2 alkyl (e.g., ethyl).

[0012] As used herein, the term "halide" refers to -Cl, -Br, -I, or -F.

[0013] As used herein, the term "non-sublimation product" refers to a product that is not the result of a process in which a substance undergoes direct transition from the solid phase to the gas phase. In some embodiments, a non-sublimation product is a product that has the properties of a non-sublimation complex.

[0014] Conventional syntheses of yttrium complexes, such as tris(alkylcyclopentadienyl)yttrium(III) complexes, require multiple steps to purify the product. For example, conventional synthetic routes use tetrahydrofuran, which coordinates with the yttrium complex and must be removed by a series of extraction and sublimation steps. The extraction and sublimation steps have the disadvantages of reducing the yield of the reactants and requiring more complex synthetic methods.

[0015] Provided herein are embodiments that, among other things, overcome the challenges and shortcomings of conventional synthesis and yttrium complexes prepared according to conventional synthesis. Some embodiments provide methods for synthesizing yttrium complexes by contacting a metal alkylcyclopentadienyl compound with a yttrium trihalide compound in a non-coordinating solvent to obtain a tris(alkylcyclopentadienyl)yttrium complex. In some embodiments, the methods disclosed herein do not involve the use of tetrahydrofuran. In some embodiments, the methods disclosed herein can achieve high yields and purity without any extraction and / or sublimation steps to purify the resulting complex. Thus, in some embodiments, the methods disclosed herein provide a simple, one-step synthetic route for producing yttrium complexes.

[0016] FIG. 1 is a flow chart of a method 100 of preparing an yttrium complex, according to some embodiments.

[0017] In step 102, in some embodiments, method 100 includes contacting a cyclopentadienyl compound with a yttrium trihalide compound in a non-coordinating solvent to obtain an yttrium complex.

[0018] In some embodiments, the contacting comprises directly contacting or placing in close proximity or proximity at least one of the cyclopentadienyl compound, the yttrium trihalide compound, the non-coordinating solvent, or any combination thereof. In some embodiments, the contacting comprises adding the cyclopentadienyl compound, the yttrium trihalide compound, and the non-coordinating solvent to a reaction vessel (e.g., a vessel, flask, vial, etc.) in any order. In some embodiments, the contacting comprises combining the cyclopentadienyl compound, the yttrium trihalide compound, and the non-coordinating solvent in a reaction vessel in any order. In some embodiments, the contacting comprises charging the cyclopentadienyl compound, the yttrium trihalide compound, and the non-coordinating solvent to a reaction vessel in any order. In some embodiments, the contacting comprises stirring the cyclopentadienyl compound, the yttrium trihalide compound, and the non-coordinating solvent. In some embodiments, the contacting comprises mixing the cyclopentadienyl compound, the yttrium trihalide compound, and the non-coordinating solvent. In some embodiments, the contacting comprises reacting a cyclopentadienyl compound, an yttrium trihalide compound, and a non-coordinating solvent.

[0019] In some embodiments, the contacting proceeds at or to a temperature in the range of 20° C. to 150° C., or any range or subrange therebetween. In some embodiments, the contacting proceeds at or to a temperature of 20°C to 140°C, 20°C to 130°C, 20°C to 120°C, 20°C to 110°C, 20°C to 100°C, 20°C to 90°C, 20°C to 80°C, 20°C to 70°C, 20°C to 60°C, 20°C to 50°C, 20°C to 40°C, 20°C to 30°C, 30°C to 150°C, 40°C to 150°C, 50°C to 150°C, 60°C to 150°C, 70°C to 150°C, 80°C to 150°C, 90°C to 150°C, 100°C to 150°C, 110°C to 150°C, 120°C to 150°C, 130°C to 150°C, or 140°C to 150°C. In some embodiments, contacting proceeds at or up to a temperature at or above the boiling point of the non-coordinating solvent.

[0020] In some embodiments, the cyclopentadienyl compound comprises a metal alkylcyclopentadienyl compound. In some embodiments, the metal alkylcyclopentadienyl compound has the following formula: [R 1 R 2 -Cp]M [In the formula, Cp is cyclopentadienyl; R 1 and R 2 are each independently hydrogen or alkyl; M is Na, Li or K].

[0021] In some embodiments, R 1 and R 2 In some embodiments, R 1 and R 2 is different.

[0022] In some embodiments, R 1 is alkyl, and R 2 is hydrogen. In some embodiments, R 1 and R 2 are each independently alkyl.

[0023] In some embodiments, the yttrium trihalide compound includes at least one of YCl3, YI3, YBr3, YF3, or any combination thereof.

[0024] In some embodiments, the non-coordinating solvent comprises a solvent that does not coordinate to any compound or complex. In some embodiments, the non-coordinating solvent comprises at least one of toluene, benzene, hexane, heptane, xylene, or any combination thereof. In some embodiments, the non-coordinating solvent does not comprise tetrahydrofuran.

[0025] In some embodiments, the yttrium complex comprises a tris(alkylcyclopentadienyl)yttrium(III) complex. In some embodiments, the yttrium complex has the following formula: TIFF2026500860000003.tif79170[In the formula, R 1 and R 2 are each independently hydrogen or alkyl.

[0026] In some embodiments, R 1 and R 2 In some embodiments, R 1 and R 2 is different.

[0027] In some embodiments, R 1 is alkyl, and R 2 is hydrogen. In some embodiments, R 1 and R 2 are each independently alkyl.

[0028] In some embodiments, the molar ratio of yttrium trichloride to cyclopentadienyl compound is 1:3 to 1:9, or any range or subrange therebetween. For example, in some embodiments, the molar ratio of yttrium trichloride to cyclopentadienyl compound is 1:3 to 1:8, 1:3 to 1:7, 1:3 to 1:6, 1:3 to 1:5, 1:3 to 1:4, 1:4 to 1:9, 1:5 to 1:9, 1:6 to 1:9, 1:7 to 1:9, or 1:8 to 1:9.

[0029] In some embodiments, the yttrium complex is not coordinated to the tetrahydrofuran.

[0030] In some embodiments, the yield of the yttrium complex is 50% to 75%, or any range or subrange therebetween, hi some embodiments, the yield of the yttrium complex is 55% to 75%, 60% to 75%, 65% to 75%, 70% to 75%, 50% to 70%, 50% to 65%, 50% to 60%, or 50% to 55%.

[0031] In step 104, in some embodiments, the method 100 includes removing at least a portion of the non-coordinating solvent to obtain a solid yttrium complex (eg, a solid-phase yttrium complex).

[0032] In some embodiments, the removing comprises a technique for separating the non-coordinating solvent from the yttrium complex. For example, in some embodiments, a cannula is used for the removing. In some embodiments, the removing comprises decanting the non-coordinating solvent to obtain the yttrium complex. In some embodiments, the removing comprises pipetting the non-coordinating solvent to obtain the yttrium complex. In some embodiments, the removing comprises pouring off the non-coordinating solvent to obtain the yttrium complex. In some embodiments, the removing comprises transferring the non-coordinating solvent to another reaction vessel to obtain the yttrium complex. In some embodiments, the removing comprises evaporating the non-coordinating solvent to obtain the yttrium complex.

[0033] In step 106, in some embodiments, the method 100 includes recrystallizing the yttrium complex.

[0034] In some embodiments, the recrystallization comprises contacting the yttrium complex with a solvent. In some embodiments, the recrystallization comprises dissolving the yttrium complex in a solvent. In some embodiments, the recrystallization comprises solubilizing the yttrium complex in a solvent. In some embodiments, the recrystallization comprises heating the yttrium complex in a solvent and then allowing the yttrium complex and solvent to cool. In some embodiments, the recrystallization comprises combining the yttrium complex and the solvent. In some embodiments, the recrystallization comprises adding the yttrium complex and the solvent. In some embodiments, the recrystallization comprises stirring the yttrium complex and the solvent. In some embodiments, the recrystallization comprises mixing the yttrium complex with the solvent. In some embodiments, the solvent comprises at least one non-coordinating solvent disclosed herein.

[0035] In some embodiments, the method 100 does not include any sublimation steps. In some embodiments, the method 100 does not include any steps involving tetrahydrofuran.

[0036] Some embodiments relate to compositions. In some embodiments, the compositions comprise or consist of an yttrium complex. In some embodiments, the yttrium complex is a complex formed in accordance with the methods disclosed herein. In some embodiments, the compositions comprise a compound represented by the following formula: TIFF2026500860000004.tif79170[In the formula, R 1 and R 2 are each independently hydrogen or alkyl.

[0037] In some embodiments, R 1 and R 2 In some embodiments, R 1 and R 2 is different.

[0038] In some embodiments, R 1 is alkyl, and R 2 is hydrogen. In some embodiments, R 1 and R 2 are each independently alkyl.

[0039] In some embodiments, the yttrium complex is not coordinated to the tetrahydrofuran.

[0040] In some embodiments, the purity of the yttrium complex is at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%, at least 96%, at least 97%, or at least 98%. In some embodiments, the purity of the yttrium complex is 70%-99%, 75%-99%, 80%-99%, 85%-99%, 90%-99%, 95%-99%, 96%-99%, 97%-99%, or 98%-99%. In some embodiments, the purity of the yttrium complex is 99% or greater. In some embodiments, the purity of the yttrium complex is 1 Determined by H NMR.

[0041] In some embodiments, the yttrium complex is a solid. In some embodiments, the composition is free of a bis(alkylcyclopentadienyl)yttrium(III) complex. In some embodiments, the composition is free of the following impurities: (RCp)Y THF; (RCp)YCl; (RCp)YCl; or any combination thereof, where R is R 1 or R 2 and Cp is cyclopentadienyl.

[0042] Comparative Example 1 Synthesis of tris(methylcyclopentadienyl)yttrium(III) complexes. As a comparative example, tris(methylcyclopentadienyl)yttrium(III) complex was synthesized from sodium methylcyclopentadiene (MeCpNa) and yttrium(III) chloride in tetrahydrofuran (THF). The synthesis involved charging MeCpNa and YCl3 (2 g) to a 250 mL Schlenk flask at room temperature with stirring under nitrogen, followed by the addition of THF. The molar ratio of YCl3 to MeCpNa was 1:4. The resulting mixture was heated to 55°C for 6 hours and then allowed to precipitate overnight. The mother liquor was transferred to another Schlenk flask via cannula. All volatiles were removed under reduced pressure. 1A yellow product of (MeCp)3Y was produced in 56% yield and 90% purity as determined by H-NMR. [Example]

[0043] Example 2 Synthesis of tris(methylcyclopentadienyl)yttrium(III) complexes. TIFF2026500860000005.tif48170 Tris(methylcyclopentadienyl)yttrium(III) complex was synthesized from sodium methylcyclopentadiene (MeCpNa) and yttrium(III) chloride in toluene. The synthesis involved charging MeCpNa and YCl3 (2 g) to a 250 mL Schlenk flask at room temperature under nitrogen with stirring, followed by the addition of toluene. The molar ratio of YCl3 to MeCpNa was 1:3. The resulting mixture was heated to 55°C for 6 hours and then allowed to settle overnight. The mother liquor was transferred to another Schlenk flask via cannula. All volatiles were removed under reduced pressure. 1 A yellow product of (MeCp)3Y was produced in 64% yield and greater than 96% purity as determined by H-NMR. Recrystallization of (MeCp)3Y from hexanes afforded 1 A purity of greater than 98% was achieved as determined by 1 H-NMR.

[0044] 1 H NMR (C6D6): 5.93ppm (m,6H,Cp-H), 5.84ppm (m,6H,Cp-H), 1.91ppm (s,9H,Cp-CH3). 13 C NMR (C6D6): 121.74, 116.39, 111.98, 14.73.

[0045] Example 3 Synthesis of tris(methylcyclopentadienyl)yttrium(III) complexes. Tris(methylcyclopentadienyl)yttrium(III) complex was synthesized from sodium methylcyclopentadiene (MeCpNa) and yttrium(III) chloride in toluene. The synthesis involved placing MeCpNa and YCl3 (2 g) in a 250 mL Schlenk flask at room temperature under nitrogen with stirring, followed by the addition of toluene. The molar ratio of YCl3 to MeCpNa was 1:4. The resulting mixture was heated to 55°C for 6 hours and then allowed to settle overnight. The mother liquor was transferred to another Schlenk flask via cannula. All volatiles were removed under reduced pressure. 1 A yellow product of (MeCp)3Y was produced in 54% yield and greater than 95% purity as determined by H-NMR. Recrystallization of (MeCp)3Y from hexanes afforded 1 A purity of greater than 98% was achieved as determined by 1 H-NMR.

[0046] Example 4 Synthesis of tris(methylcyclopentadienyl)yttrium(III) complexes. Tris(methylcyclopentadienyl)yttrium(III) complex was synthesized from sodium methylcyclopentadiene (MeCpNa) and yttrium(III) chloride in toluene. The synthesis involved placing MeCpNa and YCl3 (5 g) in a 250 mL Schlenk flask at room temperature under nitrogen with stirring, followed by the addition of toluene. The molar ratio of YCl3 to MeCpNa was 1:4. The resulting mixture was heated to 55°C for 6 hours and then allowed to settle overnight. The mother liquor was transferred to another Schlenk flask via cannula. All volatiles were removed under reduced pressure. 1 A yellow product of (MeCp)3Y was produced in 65% yield and greater than 95% purity as determined by H-NMR. Recrystallization of (MeCp)3Y from hexanes gave 1 A purity of greater than 98% was achieved as determined by 1 H-NMR.

[0047] Example 5 Synthesis of tris(methylcyclopentadienyl)yttrium(III) complexes. Tris(methylcyclopentadienyl)yttrium(III) complex was synthesized from sodium methylcyclopentadiene (MeCpNa) and yttrium(III) chloride in toluene. The synthesis involved placing MeCpNa and YCl3 (10 g) in a 250 mL Schlenk flask at room temperature under nitrogen with stirring, followed by the addition of toluene. The molar ratio of YCl3 to MeCpNa was 1:4. The resulting mixture was heated to 55°C for 6 hours and then allowed to settle overnight. The mother liquor was transferred to another Schlenk flask via cannula. All volatiles were removed under reduced pressure. 1 A yellow product of (MeCp)3Y was produced in 61% yield and greater than 96% purity as determined by H-NMR. Recrystallization of (MeCp)3Y from hexanes afforded 1 A purity of greater than 98% was achieved as determined by 1 H-NMR. TIFF2026500860000006.tif47170

[0048] Example 6 Synthesis of tris(isopropyl-methyl-cyclopentadienyl)yttrium(III) complexes Tris(dialkylcyclopentadienyl)yttrium(III) complexes are synthesized from 3-isopropyl-1-methyl-1,3-cyclopentadiene sodium (iPrMeCpNa) and yttrium(III) chloride in toluene. The synthesis involves placing iPrMeCpNa and YCl3 (10 g) in a 250 mL Schlenk flask at room temperature under nitrogen with stirring, followed by the addition of toluene. The molar ratio of YCl3 to iPrMeCpNa is 1:4. The resulting mixture is heated to 55°C for 6 hours and then allowed to precipitate overnight. The mother liquor is transferred via cannula to another Schlenk flask. All volatiles are removed under reduced pressure. 1 The yellow product (iPrMeCp)3Y is produced in greater than 50% yield and greater than 90% purity as determined by H-NMR. Recrystallization of (iPrMeCp)3Y from hexanes affords 1 A purity of greater than 98% is achieved as determined by 1 H-NMR.

[0049] Example 7 Synthesis of tris(butylcyclopentadienyl)yttrium(III) complexes. Tris(butylcyclopentadienyl)yttrium(III) complex is synthesized from sec-butyl-cyclopentadienyl sodium (sec-butyl-CpNa) and yttrium(III) chloride in toluene. The synthesis involves placing sec-butyl-CpNa and YCl3 (10 g) in a 250 mL Schlenk flask at room temperature under nitrogen with stirring, followed by the addition of toluene. The molar ratio of YCl3 to sec-butyl-CpNa is 1:4. The resulting mixture is heated to 55°C for 6 hours and then allowed to precipitate overnight. The mother liquor is transferred via cannula to another Schlenk flask. All volatiles are removed under reduced pressure. 1 The yellow product (sec-butyl-Cp)Y is produced in greater than 50% yield and greater than 90% purity as determined by H-NMR. Recrystallization of (sec-butyl-Cp)Y from hexanes affords 1 A purity of greater than 98% is achieved as determined by 1 H-NMR.

[0050] Aspects Various embodiments are described below. It should be understood that any one or more of the features listed in the following embodiments may be combined with any one or more of the other embodiments.

[0051] Aspect 1. The following formula: TIFF2026500860000007.tif79170[In the formula, R 1 and R 2 are each independently hydrogen or alkyl. A composition comprising a complex of The complex is 1 having a purity of at least 70% as determined by H NMR; The composition wherein the complex is a non-sublimation product.

[0052] Aspect 2.R1 is alkyl, and R 2 is hydrogen.

[0053] Embodiment 3. The composition according to any one of embodiments 1 to 2, wherein the alkyl is a linear alkyl.

[0054] Embodiment 4. The composition according to any one of embodiments 1 to 3, wherein the alkyl is a branched alkyl.

[0055] Aspect 5.R 1 and R 2 is each independently alkyl.

[0056] Embodiment 6. The composition according to any one of embodiments 1 to 5, wherein the alkyl is a C1 alkyl, a C3 alkyl, or a C4 alkyl.

[0057] Embodiment 7. The composition according to any one of embodiments 1 to 6, wherein the alkyl is methyl.

[0058] Embodiment 8. The composition according to any one of embodiments 1 to 7, wherein the alkyl is n-propyl or isopropyl.

[0059] Embodiment 9. The composition according to any one of embodiments 1 to 8, wherein the alkyl is n-butyl, sec-butyl, tert-butyl, or isobutyl.

[0060] Embodiment 10. The composition according to any one of embodiments 1 to 9, wherein the alkyl is methyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, or isobutyl.

[0061] Embodiment 11. The composition according to any one of embodiments 1 to 10, wherein the complex has a purity of at least 95%.

[0062] Embodiment 12. The composition according to any one of embodiments 1 to 11, wherein the complex has a purity of 95% to 99%.

[0063] Embodiment 13. The composition according to any one of embodiments 1 to 12, wherein the complex is not coordinated to tetrahydrofuran.

[0064] Aspect 14. A method of forming a compound comprising contacting a metal alkylcyclopentadienyl compound with a yttrium trihalide compound in a non-coordinating solvent to obtain a tris(alkylcyclopentadienyl)yttrium complex. A method comprising:

[0065] Aspect 15. The metal alkylcyclopentadienyl compound has the following formula: [R 1 R 2 -Cp]3M [In the formula, Cp is cyclopentadienyl; R 1 and R 2 are each independently hydrogen or alkyl; M is Na, Li, or K. 15. The method according to embodiment 14, comprising the compound of formula:

[0066] Aspect 16.R 1 is alkyl, and R 2 16. The method according to any one of embodiments 14 to 15, wherein is hydrogen.

[0067] Embodiment 17. The method according to any one of embodiments 14 to 15, wherein the alkyl is a linear alkyl.

[0068] Embodiment 18. The method according to any one of embodiments 14 to 15, wherein the alkyl is a branched alkyl.

[0069] Aspect 19.R 1 and R 2 is each independently alkyl.

[0070] Embodiment 20. The method according to any one of embodiments 14 to 15, wherein the alkyl is a C1 alkyl, a C3 alkyl, or a C4 alkyl.

[0071] Embodiment 21. The method according to any one of embodiments 14 to 15, wherein the alkyl is methyl.

[0072] Embodiment 22. The method according to any one of embodiments 14 to 15, wherein the alkyl is n-propyl or isopropyl.

[0073] Embodiment 23. The method according to any one of embodiments 14 to 15, wherein the alkyl is n-butyl, sec-butyl, tert-butyl, or isobutyl.

[0074] Embodiment 24. The method according to any one of embodiments 14 to 15, wherein the alkyl is methyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, or isobutyl.

[0075] Embodiment 25. The method according to any one of embodiments 14 to 24, wherein the yttrium trihalide compound comprises at least one of YCl3, YI3, YBr3, YF3, or any combination thereof.

[0076] Embodiment 26. The method according to any one of embodiments 14 to 25, wherein the non-coordinating solvent comprises at least one of toluene, benzene, hexane, heptane, xylene, or any combination thereof.

[0077] Embodiment 27. The method according to any one of embodiments 14 to 26, wherein the contacting proceeds at a temperature of from 20°C to 150°C.

[0078] Embodiment 28. The method according to any one of embodiments 14 to 27, wherein the non-coordinating solvent does not comprise tetrahydrofuran.

[0079] Embodiment 29. The method according to any one of embodiments 14 to 28, which does not include any sublimation step.

[0080] Aspect 30. The tris(alkylcyclopentadienyl) yttrium complex has the following formula: TIFF2026500860000008.tif79170[In the formula, R 1 and R 2 are each independently hydrogen or alkyl. 30. The method according to any one of embodiments 14 to 29, wherein

[0081] Aspect 31.R 1 is alkyl, and R 2 The method according to any one of embodiments 14 to 30, wherein is hydrogen.

[0082] Embodiment 32. The method according to any one of embodiments 14 to 30, wherein the alkyl is a linear alkyl.

[0083] Embodiment 33. The method according to any one of embodiments 14 to 30, wherein the alkyl is a branched alkyl.

[0084] Aspect 34.R 1 and R 2 is each independently alkyl.

[0085] Embodiment 35. The method according to any one of embodiments 14 to 30, wherein the alkyl is a C1 alkyl, a C3 alkyl, or a C4 alkyl.

[0086] Embodiment 36. The method according to any one of embodiments 14 to 30, wherein the alkyl is methyl.

[0087] Embodiment 37. The method according to any one of embodiments 14 to 30, wherein the alkyl is n-propyl or isopropyl.

[0088] Embodiment 38. The method according to any one of embodiments 14 to 30, wherein the alkyl is n-butyl, sec-butyl, tert-butyl, or isobutyl.

[0089] Embodiment 39. The method according to any one of embodiments 14 to 30, wherein the alkyl is methyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, or isobutyl.

[0090] Embodiment 40. The method according to any one of embodiments 14 to 30, wherein the complex has a purity of at least 95%.

[0091] Embodiment 41. The method according to any one of embodiments 14 to 30, wherein the complex has a purity of 95% to 99%.

[0092] Aspect 42. Removal of at least a portion of the non-coordinating solvent to obtain a solid-phase tris(alkylcyclopentadienyl)yttrium complex 42. The method according to any one of embodiments 14 to 41, further comprising:

[0093] It should be understood that changes in detail, particularly with respect to the materials of construction utilized and the shape, size and arrangement of parts, may be made without departing from the scope of the present disclosure. The specification and described embodiments are examples, with the true scope and spirit of the present disclosure being indicated by the claims which follow.

Claims

1. The following formula: [In the formula, R １ and R ２ are each independently hydrogen or alkyl. A composition comprising a complex of The complex is １ having a purity of at least 70% as determined by H NMR; The composition wherein the complex is a non-sublimation product.

2. R １ is alkyl, and R ２ The composition of claim 1 , wherein is hydrogen.

3. R １ and R ２ The composition of claim 1 , wherein each is independently alkyl.

4. The alkyl is C １ Alkyl, C ３ Alkyl, or C ４ The composition of claim 1 wherein the alkyl is alkyl.

5. The composition of claim 1 wherein the alkyl is methyl.

6. The composition of claim 1, wherein the alkyl is n-propyl or isopropyl.

7. The composition of claim 1, wherein the alkyl is n-butyl, sec-butyl, tert-butyl, or isobutyl.

8. 10. The composition of claim 1, wherein the complex has a purity of 95% to 99%.

9. 10. The composition of claim 1, wherein the complex is not coordinated to tetrahydrofuran.

10. A method for forming a compound comprising contacting a metal alkylcyclopentadienyl compound with a yttrium trihalide compound in a non-coordinating solvent to obtain a tris(alkylcyclopentadienyl)yttrium complex. A method comprising:

11. The metal alkylcyclopentadienyl compound has the formula: [R １ R ２ -Cp]3M [In the formula, Cp is cyclopentadienyl; R １ and R ２ are each independently hydrogen or alkyl; M is Na, Li or K.

11. The method of claim 10, comprising the compound of formula:

12. R １ is alkyl, and R ２ The method of claim 11 , wherein is hydrogen.

13. R １ and R ２ The method of claim 11 , wherein each is independently alkyl.

14. The alkyl is C １ Alkyl, C ３ Alkyl, or C ４ The method of claim 11 , wherein the alkyl is alkyl.

15. 12. The method of claim 11, wherein the alkyl is methyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, or isobutyl.

16. The yttrium trihalide compound is YCl ３ , Y.I. ３ , YBr ３ , Y.F. ３ or any combination thereof.

17. 12. The method of claim 11, wherein the non-coordinating solvent comprises at least one of toluene, benzene, hexane, heptane, xylene, or any combination thereof.

18. 12. The method of claim 11, wherein the contacting proceeds at a temperature of from 20°C to 150°C.

19. The tris(alkylcyclopentadienyl)yttrium complex has the formula: [In the formula, R １ and R ２ are each independently hydrogen or alkyl. The method of claim 11 , wherein the compound is a complex of

20. Removal of at least a portion of the non-coordinating solvent to obtain a solid-phase tris(alkylcyclopentadienyl)yttrium complex The method of claim 11 further comprising:

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