CN105622421B - 苯甲酸柱[5]芳烃酯衍生物的制备方法和应用 - Google Patents
苯甲酸柱[5]芳烃酯衍生物的制备方法和应用 Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
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- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
Abstract
本发明公开了苯甲酸柱[5]芳烃酯衍生物的制备方法和应用。所述衍生物包含柱[5]芳烃单聚体、二聚体和三聚体；所述苯甲酸柱[5]芳烃酯衍生物的制备方法是采用化学合成方法，以对甲氧基苯与多聚甲醛为起始原料，通过催化、合成反应得到产品。本产品原料简单易得、方法操作简单，反应条件温和。与常规单柱[5]芳烃由于空腔过小不能与足球烯C60发生络合作用相比，首次发现该柱[5]芳烃三聚体类化合物可通过多空腔的协同作用与足球烯C60形成主客体络合物。
Description
技术领域
本发明涉及一种苯甲酸柱[5]芳烃酯衍生物，具体是苯甲酸柱[5]芳烃酯衍生物的制备方法和应用。
技术背景
柱芳烃是由对苯二酚单元与亚甲基对位连接而成的一种新型环状主体分子，因具有高对称性、刚性和富的电子特性，对许多中性和缺电子分子客体表现出优异的主客体性能。柱芳烃在主客体化学、自组装化学和荧光化学方面的研究已备受关注。在柱[n＝5,6,7,8,9,10etc]芳烃中，柱[5]芳烃具有合成简单，原料易得，产率高等优点，其研究发展最为迅速。目前，已有大量关于柱[5]芳烃上下缘结构修饰的衍生物及主客体化学被报道。然而，由于柱[5]芳烃空腔尺寸过小，导致其作用客体类型受到较大限制，将制约了这类柱芳烃的研究发展。为了发挥柱[5]芳烃高产率的合成优势又能弥补其主客体性能的不足，我们将苯甲酰基、羧基引入到柱[5]芳烃体系合成了一种苯甲酸柱[5]芳烃酯衍生物1，期望一方面能借助甲酰基、羧基与柱芳烃空腔起到协同作用；另一方面可以通过多个柱芳烃空腔共同作用以提高其主客体络合性能。研究发现均苯三甲酸三柱[5]芳烃酯对足球烯C60具有一定的络合作用，体现了柱[5]芳烃多聚体间的协同作用，显示出苯甲酸柱[5]芳烃酯类衍生物与被公认为21世纪的"未来材料"和"革命性材料"的石墨烯进行产学研结合具有潜在的价值。
发明内容
本发明的目的是提供苯甲酸柱[5]芳烃酯衍生物的制备方法和应用。本发明产品原料廉价易得，方法操作简单，反应条件温和。
本发明解决上述技术问题的技术方案如下：
本发明采用化学合成方法，制备一种新型的苯甲酸柱[5]芳烃酯衍生物，其结构式如(I)，研究该苯甲酸柱[5]芳烃酯类化合物与足球烯C60的协同作用和识别应用，开拓柱[5]芳烃主客体化学的研究。
1.一种苯甲酸柱[5]芳烃酯衍生物，具有如下(I)的结构通式：
其中：R1，R2，R3表示甲酸柱[5]芳烃酯基、羧基、氯甲酰基、氢。
2.上述的苯甲酸柱[5]芳烃酯衍生物，其特征在于：通式(1)化合物为：
(a)1,3,5-苯三甲酸三甲基柱[5]芳烃酯；
(b)5-氯甲酰基-1,3-苯二甲酸二甲基柱[5]芳烃酯；
(c)1,3,5-苯三甲酸二甲基柱[5]芳烃酯；
(d)苯甲酸甲基柱[5]芳烃酯。
3.权利要求1所述的苯甲酸柱[5]芳烃衍酯生物，其特征在于：通过如下反应制得：
所述的反应步骤如下：
第一步，在氮气保护下，以对甲氧基苯与多聚甲醛的摩尔比1:3为原料，三氯化铁为催化剂，二氯甲烷为溶剂，在25-30℃下生成1,4-二甲氧基柱[5]芳烃；
第二步，在0～-8℃条件下干燥三氯甲烷为溶剂，在1,4-二甲氧基柱[5]芳烃中加入1-5倍摩尔量三溴化硼，生成单羟基甲基柱[5]芳烃；
第三步，在氮气保护下，单羟基甲基柱[5]芳烃溶于干燥的三氯甲烷中，与1,3,5-均三苯甲酰氯或苯甲酰氯在50～70℃条件下，以三乙胺为缚酸剂搅拌3-10小时，即得相应的苯甲酸柱[5]芳烃酯衍生物。
4.如权利要求1所述的苯甲酸柱[5]芳烃酯衍生物的应用，其特征在于：1,3,5-苯三甲酸三甲基柱[5]芳烃酯化合物作为足球烯C60识别受体的应用。
5.根据权利要求4所述的应用，所述客体为足球烯C60。
本发明优点：
1.本发明产品原料廉价易得，方法操作简单，反应条件温和。
2.本发明首次发现该柱[5]芳烃三聚体类化合物可通过多空腔的协同作用与足球烯C60形成主客体络合物。
附图说明
图1苯甲酸柱[5]芳烃酯1a与C60作用的1H NMR谱图，溶剂为CDCl3/CS2(v/v＝4:1)。
图2苯甲酸柱[5]芳烃酯1c与C60的作用1H NMR谱图，溶剂为CDCl3/CS2(v/v＝4:1)。
图3足球烯C60在不同浓度苯甲酸柱[5]芳烃酯1a的紫外谱图。
图4足球烯C60与不同浓度的苯甲酸柱[5]芳烃酯1a在409nm处紫外吸收变化图。
具体实施方式
下面结合实施例对本发明作进一步的说明，需要说明的是，下述实施例仅是用于说明，而并非限制本发明。本领域技术人员根据本发明的教导所做出的各种变化均应在本申请权利要求所要求的保护范围之内。
实施例1
苯甲酸柱[5]芳烃酯衍生物的制备方法：
在氮气保护下，向500mL两口烧瓶中依次加入1.65g(12.0mmol)1,4-二甲氧基苯、1.08g(36mmol)多聚甲醛、300mL干燥的二氯甲烷，搅拌均匀后加入0.31g(1.92mmol)无水三氯化铁，25～30℃条件下，继续反应2～3小时，TLC跟踪，反应结束后，往体系中加入150mL去离子水终止反应。然后，滤去残渣，收集有机层，用二氯甲烷萃取(50mL×3)，合并有机层，无水硫酸钠干燥过夜，柱层析分离得到1.25g白色固体1,4-二甲氧基柱[5]芳烃；在氮气保护下，向250mL两口烧瓶中依次加入490mg(0.65mmol)1,4-二甲氧基柱[5]芳烃，98mL重蒸新制的三氯甲烷，加入3A分子筛干燥剂，搅拌充分，在0～-8℃条件下，准确加入242μL(2.60mmol)BBr3，反应1.5h后，加入100mL去离子水终止反应，静置过滤，收集有机层，然后，三氯甲烷萃取(50mL×3)，合并有机相，无水硫酸钠干燥过夜，柱层析分离纯化得到265mg白色固体单羟基甲基柱[5]芳烃；在氮气保护下，向25mL的两口烧瓶中，依次加入10mL三氯甲烷、30mg(0.11mmol)1,3,5-均三苯甲酰氯或苯甲酰氯、1mL三乙胺搅拌均匀，缓慢滴加300mg(0.41mmol)2的三氯甲烷溶液，在在50～70℃下反应4小时，以TLC跟踪反应(展开剂为V乙酸乙酯:V石油醚＝1:2)，反应结束后，冷却至室温，将反应液倒入20mL去离子水，二氯甲烷萃取(10mL×3)，合并有机层，用无水硫酸钠干燥，用中低压制备色谱柱梯度洗脱，洗脱剂为V乙酸乙酯:V石油醚＝1:20增加到1:2，即得相应的苯甲酸柱[5]芳烃酯衍生物。
上述实施例中，为了此苯甲酸柱[5]芳烃酯衍生物的结构进行确证，本发明人对红外、氢谱、碳谱、质谱进行解析，确证了其结构化合物表征数据见下表1：
表1苯甲酸柱[5]芳烃酯衍生物的结构及波谱数据
实施例2
苯甲酸柱[5]芳烃酯衍生物的主客体络合选择性实施例
1.核磁检测
通过核磁1HNMR在CDCl3/CS2(v/v＝4:1)溶剂中测试法研究部分苯甲酸柱[5]芳烃酯衍生物主体分子1a、1c与客体足球烯C60的络合性能。图1是1a与足球烯C60于1:1摩尔比混合的作用谱图，发现1a中-CH2-和-OCH3基团的部分质子氢发生了0.02ppm的高场位移效应。表明该苯三甲酸三柱[5]芳烃酯能1a和足球烯C60能发生主客体络合作用；而1,3,5-苯三甲酸二甲基柱[5]芳烃酯1c却未体现出此络合性能(图2)。
2.紫外-可见(UV-vis)光谱滴定
苯三甲酸三柱[5]芳烃酯1a在[H]＝28.5×10-4mol·L-1浓度下，其紫外在400～800nm吸收较弱，未对足球烯C60在该区域的吸收产生干扰。因此，在紫外-可见光谱滴定中，固定客体C60的浓度为1×10-4mol·L-1，向体系中逐渐加入主体，考察体系在400～800nm的紫外吸收，如图3所示。随着H/G的增大，客体C60在409nm处的吸收明显增强，表明主体苯三甲酸三柱[5]芳烃酯1a能与客体C60发生相互作用，与核磁的研究结果相一致。进一步研究发现，客体C60在409nm处的吸收强度与主客体的摩尔比成一良好的线性关系如图4。表明主体苯三甲酸三柱[5]芳烃酯1a通过良好的协同作用适合于足球烯C60的紫外检测。
Claims (1)
1.苯甲酸柱[5]芳烃酯衍生物的应用，其特征在于：1,3,5-苯三甲酸三甲基柱[5]芳烃酯化合物具有如下的结构通式：
1,3,5-苯三甲酸三甲基柱[5]芳烃酯化合物作为足球烯C60识别受体的应用。
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