功能化间苯二酚杯芳烃的合成和性质研究
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摘要
作为第三代超分子化学主体的杯芳烃的分子设计和应用研究已经成为超分子化学的热点研究课题。间苯二酚杯芳烃作为主-客体化学重要的研究平台,在配位化学、分子识别、超分子自组装、分子器件、化学传感器、液晶和纳米材料等领域有广泛的应用,作为我们的杯芳烃功能化修饰、超分子自组装和配位催化性能研究课题的一部分,本文开展了以间苯二酚杯芳烃为母体的一系列功能化衍生物的合成和分子结构以及理化性质的研究,得到了一系列有意义的实验结果:
1.以甲基、邻羟基苯基和3-甲氧基-4-羟基苯基间苯二酚杯芳烃为原料,通过酰基化和烃基化等多种途径对间苯二酚杯芳烃的酚羟基进行结构修饰,合成了间苯二酚杯芳烃的乙酸酯、醚酯、磺酸酯、氯丙基和氰丙等五大类(十三种)间苯二酚杯芳烃衍生物。通过红外光谱、~1H NMR、~(13)C NMR等方法进行了结构表征,并用单晶X-Ray衍射法测定了七个间苯二酚杯芳烃衍生物的单晶分子结构。并且对分子通过氢键自组装行为进行了探讨。
2.成功开发出了一种合成关键化合物间苯二酚杯芳烃氧代乙酸酯的简洁方法,使用三氟化硼乙醚催化1,3-二(烷氧羰基甲氧基)苯和脂肪醛、芳香醛环合直接一步合成了十七种间苯二酚杯芳烃乙酸酯类化合物,通过红外光谱、~1H NMR、~(13)C NMR等方法进行了结构表征,并通过X-射线衍射得到其中三个化合物的晶体结构。
3.研究了含吡啶功能基团的间苯二酚杯芳烃的合成方法,通过间苯二酚醚酯衍生物和2-氨甲基吡啶,4-氨甲基吡啶的直接胺解反应,合成了八种间苯二酚杯芳烃吡啶酰胺衍生物;通过间苯二酚杯芳烃母体和2-, 3-,4-吡啶甲酰氯的酯化反应,合成了十二种间苯二酚杯芳烃吡啶酸酯衍生物,通过红外光谱、~1H NMR、~(13)C NMR等方法进行了结构表征,并通过X-射线衍射得到其中两个化合物的晶体结构。
4.通过间苯二酚杯芳烃醚酯衍生物与水合肼,乙二胺等二胺的胺解反应,合成了端氨基间苯二酚杯芳烃酰胺衍生物,后者与水杨醛、吡啶甲醛反应,成功的合成了一系列含8-12个亚胺功能基团的间苯二酚杯芳烃Schiff碱多齿配体,并通过红外光谱,~1H NMR对其结构进行了初步表征。
Calix[n]arenes are known as the third generation supramolecular hosters and the molecular design and chemical applications of them have become the most hot research field in supramolecular chemistry and others. Calix[4]resorcinarenes or resorcinarenes also represent an public platform of host-guest chemistry and have versatile applications in supramolecular chemistry such as coordination chemistry, molecular recognition, supramolecular self-assembly, molecular devices, chemical sensors, liquid crystal and nanomaterials. As the continuation of our research on calixarene with the aim of functional modification, supramolecular self-assembly and catalytic properties, in this text we initiated the studies on the synthesis, molecular structures and properties of some functionalized resorcinarene derivatives, and have achieved a series of significant and creative results. The main results are showed as follows:
1. With methyl, 0-hydroxyphenyl, and 3-methox-4-hydroxyphenyl resorcinarenes as starting materials and through acylation and alkylation reactions of phenolic hydroxyl groups of resorcinarenes, a series of resorcinarenes with functionalized ester, etherester, tosylate, chloropropyl, cyanopropyl groups have been synthesized. Their structures are characterized by IR, ~1H NMR and ~(13)C NMR and were further confirmed by determination of seven representative single crystals.
2. A novel and efficient method of preparation of alkyl resorcinarylacetate was successfully developed, which are key intermediates in the chemical modification of resorcinarenes. Under the catalysis of boron trifluoride etherate aliphatic or aromatic aldehydes cyclocondensated with 1,3-(dialkoxy)benzenes in methylene dichloride directly produced alkyl resorcinarylacetates in high yields. Their structures are also characterized by IR, ~1H NMR, ~(13)C NMR and confirmed by determination of three single crystals.
3. The efficient introduction methods of functional pyridyl groups into resorcinarene were investigated. Through the ammonolysis of ethyl resorcinarylacetates with 2-, 4-aminomethylpyridine in high temperature, eight resorcinarenes with functional pyridyl amide groups were prepared in satisfied yields. By esterification of reorcinarenes with 2-, 3-, 4-pyridylformyl chloride, several resorcinarenes having eight or twelve pyridylformate groups were synthesized. Their structures are fully characterized by IR, ~1H NMR, ~(13)C NMR and confirmed by determination of two single crystals.
4. Through the ammonolysis of ethyl resorcinarylacetates with hydrated hydrazine, ethylenediamine and other diaminoalkanes, resorcinarene amides with terminal free amino groups are produced. Then by the condensation reaction of the latters with salicylaldhyde, pyridinecarboaldehyde, a series of resorcinarene Schiff base ligands with eight or twelve functional imino groups have prepared efficiently. The structures of these polydentated Schiff bases were preliminarily characterized by IR, ~~1H NMR.
1.以甲基、邻羟基苯基和3-甲氧基-4-羟基苯基间苯二酚杯芳烃为原料,通过酰基化和烃基化等多种途径对间苯二酚杯芳烃的酚羟基进行结构修饰,合成了间苯二酚杯芳烃的乙酸酯、醚酯、磺酸酯、氯丙基和氰丙等五大类(十三种)间苯二酚杯芳烃衍生物。通过红外光谱、~1H NMR、~(13)C NMR等方法进行了结构表征,并用单晶X-Ray衍射法测定了七个间苯二酚杯芳烃衍生物的单晶分子结构。并且对分子通过氢键自组装行为进行了探讨。
2.成功开发出了一种合成关键化合物间苯二酚杯芳烃氧代乙酸酯的简洁方法,使用三氟化硼乙醚催化1,3-二(烷氧羰基甲氧基)苯和脂肪醛、芳香醛环合直接一步合成了十七种间苯二酚杯芳烃乙酸酯类化合物,通过红外光谱、~1H NMR、~(13)C NMR等方法进行了结构表征,并通过X-射线衍射得到其中三个化合物的晶体结构。
3.研究了含吡啶功能基团的间苯二酚杯芳烃的合成方法,通过间苯二酚醚酯衍生物和2-氨甲基吡啶,4-氨甲基吡啶的直接胺解反应,合成了八种间苯二酚杯芳烃吡啶酰胺衍生物;通过间苯二酚杯芳烃母体和2-, 3-,4-吡啶甲酰氯的酯化反应,合成了十二种间苯二酚杯芳烃吡啶酸酯衍生物,通过红外光谱、~1H NMR、~(13)C NMR等方法进行了结构表征,并通过X-射线衍射得到其中两个化合物的晶体结构。
4.通过间苯二酚杯芳烃醚酯衍生物与水合肼,乙二胺等二胺的胺解反应,合成了端氨基间苯二酚杯芳烃酰胺衍生物,后者与水杨醛、吡啶甲醛反应,成功的合成了一系列含8-12个亚胺功能基团的间苯二酚杯芳烃Schiff碱多齿配体,并通过红外光谱,~1H NMR对其结构进行了初步表征。
Calix[n]arenes are known as the third generation supramolecular hosters and the molecular design and chemical applications of them have become the most hot research field in supramolecular chemistry and others. Calix[4]resorcinarenes or resorcinarenes also represent an public platform of host-guest chemistry and have versatile applications in supramolecular chemistry such as coordination chemistry, molecular recognition, supramolecular self-assembly, molecular devices, chemical sensors, liquid crystal and nanomaterials. As the continuation of our research on calixarene with the aim of functional modification, supramolecular self-assembly and catalytic properties, in this text we initiated the studies on the synthesis, molecular structures and properties of some functionalized resorcinarene derivatives, and have achieved a series of significant and creative results. The main results are showed as follows:
1. With methyl, 0-hydroxyphenyl, and 3-methox-4-hydroxyphenyl resorcinarenes as starting materials and through acylation and alkylation reactions of phenolic hydroxyl groups of resorcinarenes, a series of resorcinarenes with functionalized ester, etherester, tosylate, chloropropyl, cyanopropyl groups have been synthesized. Their structures are characterized by IR, ~1H NMR and ~(13)C NMR and were further confirmed by determination of seven representative single crystals.
2. A novel and efficient method of preparation of alkyl resorcinarylacetate was successfully developed, which are key intermediates in the chemical modification of resorcinarenes. Under the catalysis of boron trifluoride etherate aliphatic or aromatic aldehydes cyclocondensated with 1,3-(dialkoxy)benzenes in methylene dichloride directly produced alkyl resorcinarylacetates in high yields. Their structures are also characterized by IR, ~1H NMR, ~(13)C NMR and confirmed by determination of three single crystals.
3. The efficient introduction methods of functional pyridyl groups into resorcinarene were investigated. Through the ammonolysis of ethyl resorcinarylacetates with 2-, 4-aminomethylpyridine in high temperature, eight resorcinarenes with functional pyridyl amide groups were prepared in satisfied yields. By esterification of reorcinarenes with 2-, 3-, 4-pyridylformyl chloride, several resorcinarenes having eight or twelve pyridylformate groups were synthesized. Their structures are fully characterized by IR, ~1H NMR, ~(13)C NMR and confirmed by determination of two single crystals.
4. Through the ammonolysis of ethyl resorcinarylacetates with hydrated hydrazine, ethylenediamine and other diaminoalkanes, resorcinarene amides with terminal free amino groups are produced. Then by the condensation reaction of the latters with salicylaldhyde, pyridinecarboaldehyde, a series of resorcinarene Schiff base ligands with eight or twelve functional imino groups have prepared efficiently. The structures of these polydentated Schiff bases were preliminarily characterized by IR, ~~1H NMR.
引文
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