取代基对杯芳烃上缘醛基化及杯芳烃组装纳米管的影响
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摘要
取代基效应(Substituent Effect)是分子中某些基团或原子所引起的电子效应和空间效应的总称，包括诱导效应、共轭效应、超共轭效应、场效应和空间（位阻）效应。取代基效应的影响涉及到有机化学的很多方面，包括有机化合物的物理性质、酸碱性、反应活性，有机反应的类型、速度、区域选择性及产物等。在杯芳烃化学中，利用取代基效应，不仅可以实现对杯芳烃主体分子的选择性修饰，合成一些具有特殊结构、性能的主体分子；还可以在以杯芳烃为主体的超分子自组装研究中，通过改变杯芳烃组装体上取代基的种类、空间位置、取向等，实现对组装行为的预先调控。本文利用取代基效应，对杯芳烃和硫杂杯芳烃上缘的选择性醛基化进行了研究，并通过控制取代基的种类、空间位置等，研究了取代基效应对杯芳烃构筑纳米管的影响。
第一章首先介绍了杯芳烃主体分子的结构特点及其化学修饰。其中，较为详细地介绍了普通杯芳烃和硫杂杯芳烃在多种衍生化反应中的不同之处，尤其是杯芳烃上缘的醛基化反应。分析总结了杯芳烃下缘及桥联基团的取代基效应对醛基化反应的影响。最后，介绍了基于杯芳烃组装纳米管的研究进展，分析了取代基效应在纳米管组装中的作用，并提出了本论文的选题思想。
第二章研究了取代基空间位阻效应对杯芳烃对位醛基化反应的影响。当杯芳烃下缘被两种具有不同空间位阻的烷基基团（正丙基和异丙基）取代时，受取代基尺寸和相对位置的影响，不同构象的正丙基和异丙基取代的杯芳烃上缘的空间位阻有了很大的不同。受此影响，杯芳烃衍生物的醛基化反应产物也有了一定的差异。相对于异丙基取代杯芳烃衍生物，正丙基取代的杯[4]芳烃空间位阻较小，因此无论是锥式、部分锥式还是1,3-交替构象，四个酚环都能够被完全地醛基化，且不发生脱烷基反应。对于异丙基取代杯芳烃构象异构体，其上缘空间位阻按构象1,3-交替、部分锥式、锥式逐渐增大，醛基化产物也随之变化：1,3-交替构象空间位阻最小，四醛基产物为主要产物，且不发生脱烷基反应；部分锥式位阻稍大，四醛基产物为主要产物，有两个A,B-邻位的异丙基脱去，且构象翻转为位阻较小的1,3-交替构象；锥式构象位阻最大，三醛基产物为主要产物，并且有两个A,C-对位或者三个异丙基脱去。
第三章对硫杂杯[4]芳烃上缘的选择性醛基化进行了研究。利用芳环上的取代基效应，通过控制酚羟基上取代基的种类和数目，解决了硫杂杯芳烃因硫原子的定位效应，容易生成间位取代产物的问题，成功地选择性合成了上缘不同醛基个数取代的硫杂杯[4]芳烃衍生物。对位二、三醛基硫杂杯[4]芳烃衍生物由正丙基和苯甲酰基部分取代硫杂杯[4]芳烃的醛基化得到。苯甲酰基取代的硫杂杯[4]芳烃在醛基化过程中，较长的反应时间会导致脱去一个苯甲酰基，生成下缘单取代的三醛基衍生物。采用边脱保护边醛基化的方法，以四异丙基取代的硫杂杯[4]芳烃为原料，经Duff反应可一步合成四醛基化的硫杂杯[4]芳烃。
第四章通过对杯[4]芳烃醛基衍生物的氧化，合成了一系列上缘直接连有羧基的杯[4]芳烃衍生物。如果杯芳烃的酚环被OR基团取代或者上缘连有醛基时，由于取代基的电荷效应，会降低酚环的反应活性，因而在氧化过程中，只发生醛基的氧化。然而当苯酚单元上下两端都没有取代基时，在氧化过程中，容易发生酚环自身的氧化。受羧基衍生物羧基数目以及空间取向的影响，1,3-交替构象的四醛基衍生物在氧化过程中必须加入DMSO改善溶剂对其产物的溶解能力，才能保证醛基被完全氧化。
第五章研究了取代基效应对杯芳烃组装纳米管的调控作用。杯[4]芳烃醛基衍生物因两端均没有强的氢键作用位点，在晶体状态下无法形成基于杯芳烃环腔堆积的纳米管。当其下缘为空间位阻较小的丙基时，杯芳烃倾向于利用环腔与苯环之间的π-π堆积以及CH-π相互作用组成二聚体，然后通过堆积作用以三螺旋的形式组装成纳米管结构。如果杯芳烃下缘的取代基为两个位阻较大的苯甲酰基，环腔结构就会因为取代苯环的上缘的紧缩被堵塞，此时无法形成二聚体结构，杯芳烃则通过π-π相互作用组装成一个圆盘状的六聚体，通过盘面的密堆积形成纳米管。只有一端连有羧酸的杯芳烃衍生物在发生自组装时，依然无法形成基于环腔堆积的纳米管，此时杯芳烃倾向于形成一维的链状结构。当杯芳烃两端均被羧基取代时，在不同的结晶条件下，杯芳烃均倾向于形成基于环腔堆积组装的纳米管结构。
Substituent effects, including inductive effect, conjugation effect, hyperconjugation effect,field effect and steric effect, are the generic term for electronic effects and steric effect causedby groups or atoms of the molecules. Substituent effects related to many aspects of organicchemistry, including the physical properties, pH, reactivity of the organic compounds and theorganic reaction types, speed, region selectivity, and products. In calixarene chemistry,substituent effects can be used not only to synthesize host molecules with special structuresand properties by selective modification of calixarenes, but to control the self-assembly ofcalixarenes by changing the types, spatial location, orientation of the substituents. In thispaper, the effects of substituents on the formylations of calixarene and thiacalixarene on theupper rim and the constructions of calixarene nanotubes were studied.
In chapter one, the structural characteristics and modifications of calixarenes wereintroduced. The differences of functionalizations of calixarene and thiacalixarene wereexpounded, especially that of the formylation reactions. The effects of substituents on thelower rim and bridging groups in the formylation reactions of calixarens were analyzed andsummarized. In the end, the nanotubes formed by the self-assembly of calixarenes werereviewed. And the effect of substituents in nanotube assembly was analyzed. In light of theabove introduction, the design strategies of this thesis are outlined.
In chapter two, the influences of steric effects of substituents on the formylations ofcalixarenes were studied. The steric hinderance of the upper rims of calixarene derivatives indifferent conformations, which were synthesized by introduing propyl or isopropyl groups tothe lower rims, was greatly different due to the different sizes and orientations of substituents.Compared with isopropoxy calixarenes, the steric hinderance effect of propoxy calixarenes ismuch weaker. Therefore, tetrapropoxy compounds in all conformations could be smoothlytransformed into the corresponding tetraformyl derivatives and no alkyl group wasdealkylated. For the tetraisopropoxy calixarenes, with the increase of steric hinderance,1,3-alternate conformer gave exhaustively formylated product with no alkyl groupdealkylating; partial cone conformer gave the tetraformylated proximal A,B-diether in1,3-alternate conformation; and cone conformer led to triformylated derivatives accompaniedby the selective dealkylations of three or two diametrical alkyl groups.
In chapter three, the selective formylations of thiacalix[4]arene on the upper rim werestudied. Influenced by the orientation effect of S atoms, thiacalixarene always give metasubstitutions. The selective syntheses of formylated thiacalix[4]arenes on the para positionswere successfully achieved by controlling the types and numbers of the substituents towardthe OH groups of the phenol rings. Di-and triformylated thiacalix[4]arenes were obtained byformylation of partially propyl-or benzoyl-substituted thiacalix[4]arenes. Prolonged reactiontimes resulted in the hydrolysis of one of the benzoyl groups of dibenzoxythiacalix[4]arene togive a triformylated product. Inspired by this, Complete para-formylation was successfullyachieved by formylation and dealkylation of tetraisopropoxythiacalix[4]arene conformers in one step.
In chapter four, a series of calix[4]arene derivatives bearing carboxyl groups directly onthe upper rims were synthesized by the oxidation of formylated calix[4]arenes. If the phenolrings of the calixarenes were substituted by OR groups or formyl groups, affected by theelectronic effects of substituents, the reactivity of the rings would decrease, and only formylgroups would be oxidized. However, if the phenol rings were not substituted on either rim, therings itselves would be oxidized. Influenced by the number and orientations of carboxylgroups, in order to obtain completely oxidized products, in the oxidation process oftetraformylated calixarenes in1,3-alternate conformation, DMSO must be added to increasethe solubility of the products.
In chapter five, the effects of substituents on the constructions of calixarene nanotubeswere studied. The nanotubes formed by the stacking of the calixarene cavities cann't beobtained by using formylated calix[4]arenes due to the absence of strong hydrogen-bondinggroups. The formylated calix[4]arenes, of which the lower rims were substituted by propylgroups, tended to form dimers under interactions of CH-π and π-π stacking. And thenanotubes were constructed under stacking interactions in a triple helix form. When the lowerrim of calixarene was substituted by benzoxy groups, the cavity of the calixarene would beccupied by the inwardly orientated phenol rings and the dimer could not form. In the solidstate, dibenzoxycalix[4]arene diformyl derivative formed a hexamer ring under π-πinteractions. Nanotube was formed by the stacking of the hexamer rings. In the self-assemblyof calix[4]arene derivatives bearing carboxyl groups only on one side, one-dimensional chainarchitectures were constrcted. The1,3-alternate calix[4]arene derivatives bearing carboxylgroups on either side, in different crystallization medium, always form nanotubes by thestacking of the calixarene cavities.
第一章首先介绍了杯芳烃主体分子的结构特点及其化学修饰。其中，较为详细地介绍了普通杯芳烃和硫杂杯芳烃在多种衍生化反应中的不同之处，尤其是杯芳烃上缘的醛基化反应。分析总结了杯芳烃下缘及桥联基团的取代基效应对醛基化反应的影响。最后，介绍了基于杯芳烃组装纳米管的研究进展，分析了取代基效应在纳米管组装中的作用，并提出了本论文的选题思想。
第二章研究了取代基空间位阻效应对杯芳烃对位醛基化反应的影响。当杯芳烃下缘被两种具有不同空间位阻的烷基基团（正丙基和异丙基）取代时，受取代基尺寸和相对位置的影响，不同构象的正丙基和异丙基取代的杯芳烃上缘的空间位阻有了很大的不同。受此影响，杯芳烃衍生物的醛基化反应产物也有了一定的差异。相对于异丙基取代杯芳烃衍生物，正丙基取代的杯[4]芳烃空间位阻较小，因此无论是锥式、部分锥式还是1,3-交替构象，四个酚环都能够被完全地醛基化，且不发生脱烷基反应。对于异丙基取代杯芳烃构象异构体，其上缘空间位阻按构象1,3-交替、部分锥式、锥式逐渐增大，醛基化产物也随之变化：1,3-交替构象空间位阻最小，四醛基产物为主要产物，且不发生脱烷基反应；部分锥式位阻稍大，四醛基产物为主要产物，有两个A,B-邻位的异丙基脱去，且构象翻转为位阻较小的1,3-交替构象；锥式构象位阻最大，三醛基产物为主要产物，并且有两个A,C-对位或者三个异丙基脱去。
第三章对硫杂杯[4]芳烃上缘的选择性醛基化进行了研究。利用芳环上的取代基效应，通过控制酚羟基上取代基的种类和数目，解决了硫杂杯芳烃因硫原子的定位效应，容易生成间位取代产物的问题，成功地选择性合成了上缘不同醛基个数取代的硫杂杯[4]芳烃衍生物。对位二、三醛基硫杂杯[4]芳烃衍生物由正丙基和苯甲酰基部分取代硫杂杯[4]芳烃的醛基化得到。苯甲酰基取代的硫杂杯[4]芳烃在醛基化过程中，较长的反应时间会导致脱去一个苯甲酰基，生成下缘单取代的三醛基衍生物。采用边脱保护边醛基化的方法，以四异丙基取代的硫杂杯[4]芳烃为原料，经Duff反应可一步合成四醛基化的硫杂杯[4]芳烃。
第四章通过对杯[4]芳烃醛基衍生物的氧化，合成了一系列上缘直接连有羧基的杯[4]芳烃衍生物。如果杯芳烃的酚环被OR基团取代或者上缘连有醛基时，由于取代基的电荷效应，会降低酚环的反应活性，因而在氧化过程中，只发生醛基的氧化。然而当苯酚单元上下两端都没有取代基时，在氧化过程中，容易发生酚环自身的氧化。受羧基衍生物羧基数目以及空间取向的影响，1,3-交替构象的四醛基衍生物在氧化过程中必须加入DMSO改善溶剂对其产物的溶解能力，才能保证醛基被完全氧化。
第五章研究了取代基效应对杯芳烃组装纳米管的调控作用。杯[4]芳烃醛基衍生物因两端均没有强的氢键作用位点，在晶体状态下无法形成基于杯芳烃环腔堆积的纳米管。当其下缘为空间位阻较小的丙基时，杯芳烃倾向于利用环腔与苯环之间的π-π堆积以及CH-π相互作用组成二聚体，然后通过堆积作用以三螺旋的形式组装成纳米管结构。如果杯芳烃下缘的取代基为两个位阻较大的苯甲酰基，环腔结构就会因为取代苯环的上缘的紧缩被堵塞，此时无法形成二聚体结构，杯芳烃则通过π-π相互作用组装成一个圆盘状的六聚体，通过盘面的密堆积形成纳米管。只有一端连有羧酸的杯芳烃衍生物在发生自组装时，依然无法形成基于环腔堆积的纳米管，此时杯芳烃倾向于形成一维的链状结构。当杯芳烃两端均被羧基取代时，在不同的结晶条件下，杯芳烃均倾向于形成基于环腔堆积组装的纳米管结构。
Substituent effects, including inductive effect, conjugation effect, hyperconjugation effect,field effect and steric effect, are the generic term for electronic effects and steric effect causedby groups or atoms of the molecules. Substituent effects related to many aspects of organicchemistry, including the physical properties, pH, reactivity of the organic compounds and theorganic reaction types, speed, region selectivity, and products. In calixarene chemistry,substituent effects can be used not only to synthesize host molecules with special structuresand properties by selective modification of calixarenes, but to control the self-assembly ofcalixarenes by changing the types, spatial location, orientation of the substituents. In thispaper, the effects of substituents on the formylations of calixarene and thiacalixarene on theupper rim and the constructions of calixarene nanotubes were studied.
In chapter one, the structural characteristics and modifications of calixarenes wereintroduced. The differences of functionalizations of calixarene and thiacalixarene wereexpounded, especially that of the formylation reactions. The effects of substituents on thelower rim and bridging groups in the formylation reactions of calixarens were analyzed andsummarized. In the end, the nanotubes formed by the self-assembly of calixarenes werereviewed. And the effect of substituents in nanotube assembly was analyzed. In light of theabove introduction, the design strategies of this thesis are outlined.
In chapter two, the influences of steric effects of substituents on the formylations ofcalixarenes were studied. The steric hinderance of the upper rims of calixarene derivatives indifferent conformations, which were synthesized by introduing propyl or isopropyl groups tothe lower rims, was greatly different due to the different sizes and orientations of substituents.Compared with isopropoxy calixarenes, the steric hinderance effect of propoxy calixarenes ismuch weaker. Therefore, tetrapropoxy compounds in all conformations could be smoothlytransformed into the corresponding tetraformyl derivatives and no alkyl group wasdealkylated. For the tetraisopropoxy calixarenes, with the increase of steric hinderance,1,3-alternate conformer gave exhaustively formylated product with no alkyl groupdealkylating; partial cone conformer gave the tetraformylated proximal A,B-diether in1,3-alternate conformation; and cone conformer led to triformylated derivatives accompaniedby the selective dealkylations of three or two diametrical alkyl groups.
In chapter three, the selective formylations of thiacalix[4]arene on the upper rim werestudied. Influenced by the orientation effect of S atoms, thiacalixarene always give metasubstitutions. The selective syntheses of formylated thiacalix[4]arenes on the para positionswere successfully achieved by controlling the types and numbers of the substituents towardthe OH groups of the phenol rings. Di-and triformylated thiacalix[4]arenes were obtained byformylation of partially propyl-or benzoyl-substituted thiacalix[4]arenes. Prolonged reactiontimes resulted in the hydrolysis of one of the benzoyl groups of dibenzoxythiacalix[4]arene togive a triformylated product. Inspired by this, Complete para-formylation was successfullyachieved by formylation and dealkylation of tetraisopropoxythiacalix[4]arene conformers in one step.
In chapter four, a series of calix[4]arene derivatives bearing carboxyl groups directly onthe upper rims were synthesized by the oxidation of formylated calix[4]arenes. If the phenolrings of the calixarenes were substituted by OR groups or formyl groups, affected by theelectronic effects of substituents, the reactivity of the rings would decrease, and only formylgroups would be oxidized. However, if the phenol rings were not substituted on either rim, therings itselves would be oxidized. Influenced by the number and orientations of carboxylgroups, in order to obtain completely oxidized products, in the oxidation process oftetraformylated calixarenes in1,3-alternate conformation, DMSO must be added to increasethe solubility of the products.
In chapter five, the effects of substituents on the constructions of calixarene nanotubeswere studied. The nanotubes formed by the stacking of the calixarene cavities cann't beobtained by using formylated calix[4]arenes due to the absence of strong hydrogen-bondinggroups. The formylated calix[4]arenes, of which the lower rims were substituted by propylgroups, tended to form dimers under interactions of CH-π and π-π stacking. And thenanotubes were constructed under stacking interactions in a triple helix form. When the lowerrim of calixarene was substituted by benzoxy groups, the cavity of the calixarene would beccupied by the inwardly orientated phenol rings and the dimer could not form. In the solidstate, dibenzoxycalix[4]arene diformyl derivative formed a hexamer ring under π-πinteractions. Nanotube was formed by the stacking of the hexamer rings. In the self-assemblyof calix[4]arene derivatives bearing carboxyl groups only on one side, one-dimensional chainarchitectures were constrcted. The1,3-alternate calix[4]arene derivatives bearing carboxylgroups on either side, in different crystallization medium, always form nanotubes by thestacking of the calixarene cavities.
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