[5+1]关环法合成锇苯和钌苯的研究
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摘要
含过渡金属的有机共轭体系以其特殊的分子结构、化学与物理性能,在金属有机化学中居重要地位。本论文合成了一系列新颖的钌苯、锇苯及其相关化合物,对其进行全面表征,同时对于它们的反应活性及物理性能进行初步研究。
本论文共分为六章,包括金属苯的研究进展;锇苯及其衍生物的合成及表征;锇杂呋喃的合成及表征;钌苯的合成及表征;钌苯的化学与物理性能研究;论文的创新性和研究工作的展望。
第一章为绪论,评述了金属苯领域中已取得的研究成果及其在过渡金属有机化学研究中的地位。简要介绍了金属苯的定义和已报道的金属苯的几种合成方法,同时结合本论文的核心部分,介绍了由第一、第二过渡系金属构筑的金属苯及其相关化合物的研究进展。
第二章主要研究锇苯及其衍生物的合成和表征。本章利用高反应活性的锇配合物Os(CHC(PPh_3)CH(OH)CCH)Cl_2(PPh_3)_2为原料,与亲核试剂NaSCN及NaX反应,分离得到两种结构新颖的芳杂环上带有官能团的锇苯Os(CHC(PPh_3)CHC(SCN)CH)(SCN)_2(PPh_3)_2和Os(CHC(PPh_3)CHCICH)I_2(PPh_3)_2。同时,从上述反应中还分离到两种具有α,β-不饱和酮式结构的锇配合物Os(CHC(PPh_3)COCHCH_2)(SCN)_2(PPh_3)_2和Os(CHC(PPh_3)COCHCH_2)Br_2(PPh_3)_2。此外,采用多种配体,研究了锇苯[Os(CHC(PPh_3)CHC(PPh_3)CH)Cl_2(PPh_3)_2]OH的取代反应性,制备了一系列锇苯衍生物。
第三章主要研究锇杂呋喃的合成和表征。本章以锇氢化合物OsHCl(Co)(PPh_3)_3为原料,与HC≡CCH(OH)C≡CH反应,合成了稳定的锇杂呋喃[Os(CHC(PPh_3)C(CH_2CH_3)O)Cl(CO)(PPh_3)_2],并对其进行了系统的表征。
第四章主要研究非配位型稳定钌苯的合成及表征。利用配位不饱和化合物RuCl_2(PPh_3)_3为原料,与HC≡CCH(OH)C≡CH反应,一锅法合成了首例稳定的非配位型钌苯[Ru(CHC(PPh_3)CHC(PPh_3)CH)Cl_2(PPh_3)_2]Cl,并对其结构进行了系统的表征。此方面研究成果打破了以往普遍认为的“由第一、第二过渡系金属构筑的金属苯是不稳定的”的论断,对金属苯领域的深入研究具有积极意义。为了推测钌苯的合成反应机理,在该反应中有意引入酸性介质,并对反应的主要副产物进行分离和表征。此外,还首次验证了以无机盐(RuCl_3)为原料进行直接一锅法合成金属苯的可行性。
第五章主要开展钌苯的性能研究工作。采用多种配体,系统研究了钌苯[Ru(CHC(PPh_3)CHC(PPh_3)CH)Cl_2(PPh_3)_2]Cl的取代反应性,制备了一系列结构新颖的钌苯配合物。配体取代反应研究结果表明:钌苯的反应活性比具有相似结构的锇苯大得多。对于同种配体的取代,锇苯往往需要比钌苯更强的反应条件。此外,在钌苯的性能研究方面,除了深入研究钌苯热稳定性,分离表征了其热分解产物外,对钌苯的发光规律也进行了考察。研究了联吡啶类双齿配体取代的两例钌苯对一些具有配位能力的重要生命物种(如糖类、核苷和及氨基酸等)的光学响应情况,发现钌苯[Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)(C_(12)H_8N_2)Cl]Cl_2对半胱氨酸有显著的特征性荧光和吸收响应。对荧光响应产物进行分离,得到首例含氨基酸配体的金属苯。同时,研究发现钌苯[Ru(CHC(PPh_3)CHC(PPh_3)CH)-Cl_2(PPh_3)_2]Cl对重要生理标示物种——硫氰酸根的也具有特殊的荧光响应,并成功地对响应产物进行了分离和表征。
第六章总结了本论文研究工作的创新性,并提出了本工作的后续研究思路。
Transition-metal-containing conjugated organometallic complexes play an important role in organometallic chemistry research because they can exhibit special structural and chemical properties as well as physical properties.In this dissertation, the synthesis and characterization of several novel ruthenabenzenes,osmabenzenes and related complexes have been described.The reactivities and properties of these complexes have also been studied.
This dissertation consists of six chapters:research progress in metallabenzenes; synthesis and characterization of osmabenzenes and related complexes;synthesis and characterization of osmafuran;synthesis and characterization of ruthenabenzenes; chemical and physical properties of ruthenabenzenes;conclusion and prospect.
In chapter 1,the research progress of metallabenzenes are reviewed.In this chapter,the definition of metallabenzenes and the reported synthetic methods of metallabenzenes are briefly introduced.According to the main objective of this dissertation,the research progress of metallabenzenes with the metal centre of the first and the second transition series is also reviewed in this chapter.In addition,the research objectives of this dissertation are presented.
In chapter 2,the synthesis and characterization of osmabenzenes and the related complexes are described.The complex Os(CHC(PPh_3)CH(OH)CCH)Cl_2(PPh_3)_2 reacts with nucleophiles SCN~- and X~- to give the unusual osmabenzenes Os(CH-C(PPh_3)CHC(SCN)CH)(SCN)_2(PPh_3)_2 and Os(CHC(PPh_3)CHCICH)I_2(PPh_3)_2 with reactive groups on the metallacycles.Furthermore,twoα,β-unsaturated ketone complexes are obtained from the reactions and well characterized.Treatment of osmabenzene[Os(CHC(PPh_3)CHC(PPh_3)CH)Cl_2(PPh_3)_2]OH with some ligands lead to the isolation of several stable osmabenzenes.
In chapter 3,the stable osmafuran Os(CHC(PPh_3)C(CH_2CH_3)O)Cl(CO)(PPh_3)_2 are synthesized and characterized.Reaction of OsHCl(CO)(PPh_3)_3 with HC≡CCH(OH)C=CH afforded the stable osmafuran Os(CHC(PPh_3)C(CH_2CH_3)O)-Cl(CO)(PPh_3)_2.
Chapter 4 describes the research work on the synthesis and characterization of non-metal-coordinated ruthenabenzenes.Treatment of RuCl_2(PPh_3)_3 with HC≡CCH(OH)C≡CH,Bu_4NCl and PPh_3 at room temperature by one pot reaction produces the first stable non-metal-coordinated ruthenabenzene [Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)_2-Cl_2]Cl in good yield.This result shattered the former expectation that the synthetic edfforts to prepare an isolable metallabenzene of a 4d metal which is not coordinated to another metal fragment would be futile,which will expand the research field of metallabenzenes.To study the plausible mechanism for the formation of ruthenabenzene,the reaction is carried out in presence of purposely added AcOH,and the byproduct [Ru(CO)(CHC(PPh_3)CHCH_2)(CH_3COO)(PPh_3)_2]Cl is isolated and characterized.The ruthenabenzene can even be obtained from the one-pot reaction of RuCl_3,PPh_3,and HC≡CCH(OH)C≡CH in CHCl_3,although the yield is lower.
Chapter 5 describes the property studies of ruthenabenzenes.Ligand substitution reactions of the ruthenabenzene with several ligands produce a series of stable ruthenabenznes with special property.Ligand substitution reactions of the ruthenabenzene indicate that the ruthenabenzene is more reactive compared to the osmabenzene with similar structure.During the further investigation of the thermal stability of the ruthenabenzene,the dominant thermal decomposition products are isolated and well characterized.In addition,the optical response of ruthenabenzenes [Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)(C_(10)H_8N_2)Cl]Cl_2 and[Ru(CHC(PPh_3)CH-C(PPh_3)CH)(PPh_3)(C_(12)H_8N_2)Cl]Cl_2 with a wide range of external stimulus including physiological anions,glucose,nucleoside analogues andα-amino acids have been investigated.In tests of ruthenabcnzcne[Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)-(C_(12)H_8N_2)Cl]Cl_2 with sulfhydryl-containing amino acids,cysteine is recognised by remarkable fluorescence or absorption changes.The response product is isolated and characterized as the fist mctallabenzene containing amino acid ligand.Further study shows that titration of ruthenabenzene[Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)2Cl_2]Cl with thiocyanate ion also resulted in special fluorescence response,which afford the ruthenabenzene product[Ru(CHC(PPh_3)CHC(PPh_3)CH)(SCN)_2(PPh_3)_2]Cl.
In the final part of the dissertation,chapter 6,the innovation of the dissertation is concluded and the prospect of this research is presented.
本论文共分为六章,包括金属苯的研究进展;锇苯及其衍生物的合成及表征;锇杂呋喃的合成及表征;钌苯的合成及表征;钌苯的化学与物理性能研究;论文的创新性和研究工作的展望。
第一章为绪论,评述了金属苯领域中已取得的研究成果及其在过渡金属有机化学研究中的地位。简要介绍了金属苯的定义和已报道的金属苯的几种合成方法,同时结合本论文的核心部分,介绍了由第一、第二过渡系金属构筑的金属苯及其相关化合物的研究进展。
第二章主要研究锇苯及其衍生物的合成和表征。本章利用高反应活性的锇配合物Os(CHC(PPh_3)CH(OH)CCH)Cl_2(PPh_3)_2为原料,与亲核试剂NaSCN及NaX反应,分离得到两种结构新颖的芳杂环上带有官能团的锇苯Os(CHC(PPh_3)CHC(SCN)CH)(SCN)_2(PPh_3)_2和Os(CHC(PPh_3)CHCICH)I_2(PPh_3)_2。同时,从上述反应中还分离到两种具有α,β-不饱和酮式结构的锇配合物Os(CHC(PPh_3)COCHCH_2)(SCN)_2(PPh_3)_2和Os(CHC(PPh_3)COCHCH_2)Br_2(PPh_3)_2。此外,采用多种配体,研究了锇苯[Os(CHC(PPh_3)CHC(PPh_3)CH)Cl_2(PPh_3)_2]OH的取代反应性,制备了一系列锇苯衍生物。
第三章主要研究锇杂呋喃的合成和表征。本章以锇氢化合物OsHCl(Co)(PPh_3)_3为原料,与HC≡CCH(OH)C≡CH反应,合成了稳定的锇杂呋喃[Os(CHC(PPh_3)C(CH_2CH_3)O)Cl(CO)(PPh_3)_2],并对其进行了系统的表征。
第四章主要研究非配位型稳定钌苯的合成及表征。利用配位不饱和化合物RuCl_2(PPh_3)_3为原料,与HC≡CCH(OH)C≡CH反应,一锅法合成了首例稳定的非配位型钌苯[Ru(CHC(PPh_3)CHC(PPh_3)CH)Cl_2(PPh_3)_2]Cl,并对其结构进行了系统的表征。此方面研究成果打破了以往普遍认为的“由第一、第二过渡系金属构筑的金属苯是不稳定的”的论断,对金属苯领域的深入研究具有积极意义。为了推测钌苯的合成反应机理,在该反应中有意引入酸性介质,并对反应的主要副产物进行分离和表征。此外,还首次验证了以无机盐(RuCl_3)为原料进行直接一锅法合成金属苯的可行性。
第五章主要开展钌苯的性能研究工作。采用多种配体,系统研究了钌苯[Ru(CHC(PPh_3)CHC(PPh_3)CH)Cl_2(PPh_3)_2]Cl的取代反应性,制备了一系列结构新颖的钌苯配合物。配体取代反应研究结果表明:钌苯的反应活性比具有相似结构的锇苯大得多。对于同种配体的取代,锇苯往往需要比钌苯更强的反应条件。此外,在钌苯的性能研究方面,除了深入研究钌苯热稳定性,分离表征了其热分解产物外,对钌苯的发光规律也进行了考察。研究了联吡啶类双齿配体取代的两例钌苯对一些具有配位能力的重要生命物种(如糖类、核苷和及氨基酸等)的光学响应情况,发现钌苯[Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)(C_(12)H_8N_2)Cl]Cl_2对半胱氨酸有显著的特征性荧光和吸收响应。对荧光响应产物进行分离,得到首例含氨基酸配体的金属苯。同时,研究发现钌苯[Ru(CHC(PPh_3)CHC(PPh_3)CH)-Cl_2(PPh_3)_2]Cl对重要生理标示物种——硫氰酸根的也具有特殊的荧光响应,并成功地对响应产物进行了分离和表征。
第六章总结了本论文研究工作的创新性,并提出了本工作的后续研究思路。
Transition-metal-containing conjugated organometallic complexes play an important role in organometallic chemistry research because they can exhibit special structural and chemical properties as well as physical properties.In this dissertation, the synthesis and characterization of several novel ruthenabenzenes,osmabenzenes and related complexes have been described.The reactivities and properties of these complexes have also been studied.
This dissertation consists of six chapters:research progress in metallabenzenes; synthesis and characterization of osmabenzenes and related complexes;synthesis and characterization of osmafuran;synthesis and characterization of ruthenabenzenes; chemical and physical properties of ruthenabenzenes;conclusion and prospect.
In chapter 1,the research progress of metallabenzenes are reviewed.In this chapter,the definition of metallabenzenes and the reported synthetic methods of metallabenzenes are briefly introduced.According to the main objective of this dissertation,the research progress of metallabenzenes with the metal centre of the first and the second transition series is also reviewed in this chapter.In addition,the research objectives of this dissertation are presented.
In chapter 2,the synthesis and characterization of osmabenzenes and the related complexes are described.The complex Os(CHC(PPh_3)CH(OH)CCH)Cl_2(PPh_3)_2 reacts with nucleophiles SCN~- and X~- to give the unusual osmabenzenes Os(CH-C(PPh_3)CHC(SCN)CH)(SCN)_2(PPh_3)_2 and Os(CHC(PPh_3)CHCICH)I_2(PPh_3)_2 with reactive groups on the metallacycles.Furthermore,twoα,β-unsaturated ketone complexes are obtained from the reactions and well characterized.Treatment of osmabenzene[Os(CHC(PPh_3)CHC(PPh_3)CH)Cl_2(PPh_3)_2]OH with some ligands lead to the isolation of several stable osmabenzenes.
In chapter 3,the stable osmafuran Os(CHC(PPh_3)C(CH_2CH_3)O)Cl(CO)(PPh_3)_2 are synthesized and characterized.Reaction of OsHCl(CO)(PPh_3)_3 with HC≡CCH(OH)C=CH afforded the stable osmafuran Os(CHC(PPh_3)C(CH_2CH_3)O)-Cl(CO)(PPh_3)_2.
Chapter 4 describes the research work on the synthesis and characterization of non-metal-coordinated ruthenabenzenes.Treatment of RuCl_2(PPh_3)_3 with HC≡CCH(OH)C≡CH,Bu_4NCl and PPh_3 at room temperature by one pot reaction produces the first stable non-metal-coordinated ruthenabenzene [Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)_2-Cl_2]Cl in good yield.This result shattered the former expectation that the synthetic edfforts to prepare an isolable metallabenzene of a 4d metal which is not coordinated to another metal fragment would be futile,which will expand the research field of metallabenzenes.To study the plausible mechanism for the formation of ruthenabenzene,the reaction is carried out in presence of purposely added AcOH,and the byproduct [Ru(CO)(CHC(PPh_3)CHCH_2)(CH_3COO)(PPh_3)_2]Cl is isolated and characterized.The ruthenabenzene can even be obtained from the one-pot reaction of RuCl_3,PPh_3,and HC≡CCH(OH)C≡CH in CHCl_3,although the yield is lower.
Chapter 5 describes the property studies of ruthenabenzenes.Ligand substitution reactions of the ruthenabenzene with several ligands produce a series of stable ruthenabenznes with special property.Ligand substitution reactions of the ruthenabenzene indicate that the ruthenabenzene is more reactive compared to the osmabenzene with similar structure.During the further investigation of the thermal stability of the ruthenabenzene,the dominant thermal decomposition products are isolated and well characterized.In addition,the optical response of ruthenabenzenes [Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)(C_(10)H_8N_2)Cl]Cl_2 and[Ru(CHC(PPh_3)CH-C(PPh_3)CH)(PPh_3)(C_(12)H_8N_2)Cl]Cl_2 with a wide range of external stimulus including physiological anions,glucose,nucleoside analogues andα-amino acids have been investigated.In tests of ruthenabcnzcne[Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)-(C_(12)H_8N_2)Cl]Cl_2 with sulfhydryl-containing amino acids,cysteine is recognised by remarkable fluorescence or absorption changes.The response product is isolated and characterized as the fist mctallabenzene containing amino acid ligand.Further study shows that titration of ruthenabenzene[Ru(CHC(PPh_3)CHC(PPh_3)CH)(PPh_3)2Cl_2]Cl with thiocyanate ion also resulted in special fluorescence response,which afford the ruthenabenzene product[Ru(CHC(PPh_3)CHC(PPh_3)CH)(SCN)_2(PPh_3)_2]Cl.
In the final part of the dissertation,chapter 6,the innovation of the dissertation is concluded and the prospect of this research is presented.
引文
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