氧化石墨烯表面功能化修饰
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摘要
作为一种新兴碳材料，石墨烯具有独特的力学，光学，热学和电学性能，例如反常的量子霍尔效应，高的杨氏模量，高热导率和高比表面积等。正是由于石墨烯的这些优异的性能，它被广泛应用于制备各类功能性的纳米复合材料，在电子学，光学，催化等领域内具有广阔的应用前景。然而，石墨烯的工业化应用还存在诸多困难，规模化制备石墨烯便是主要的挑战之一。氧化石墨烯因与石墨烯在结构上非常类似而通常被当做制备石墨烯的前驱体，采用热处理或者化学还原氧化石墨烯的方式可以有效地规模化制备石墨烯，特别是通过化学方式修饰氧化石墨烯的途径众多，具有较高的学术研究价值。本论文主要对氧化石墨烯的表面修饰展开研究，主要研究内容包括：
1)有机小分子对氧化石墨烯的表面改性。以三聚氰氯为原料合成了有机小分子2-氨基-4，6-双十二胺-1，3，5-三嗪(ADDT)，合成产物ADDT的化学结构经傅里叶红外(FT-IR）谱和核磁共振谱1H NMR得以确定。随后对合成产物的热稳定性进行了研究，从热重分析(TGA)的结果来看，制备的ADDT相对于三聚氰胺来说具有更高的热稳定性，其分解温度范围与聚合物的分解温度范围有较大的重合。为了将ADDT以共价键的方式接枝在氧化石墨烯的表面，氧化石墨烯先与二氯亚砜反应，将表面的羧基转化为酰氯基，然后ADDT与酰氯化氧化石墨烯反应。产物GO-ADDT经FT-IR、X射线光电子能谱(XPS)和高分辨透射电镜（HRTEM）表征，确认ADDT通过酰胺键接枝在氧化石墨烯片的表面上，随后对GO-ADDT的热稳定性和溶解性进行了考察。从TGA的结果来看，接枝上ADDT之后，产物的热稳定有了明显提高，随着温度的升高其质量损失速率明显降低且GO-ADDT最后的残余量要明显高于氧化石墨。将产物GO-ADDT分散在氯仿和水的混合溶剂中，接枝后的产物表现出明显的疏水性，在氯仿中能很好的分散，这说明在改性之后，氧化石墨烯的表面由亲水转为疏水，这种变化将为GO-ADDT应用于非极性聚合物基复合材料打下基础。
2）在温和的条件下，一步法同时还原银离子和氧化石墨烯制得石墨烯/纳米银复合材料。在实验中，以甲醛为还原剂，聚乙烯吡咯烷酮(PVP)为保护剂，经过7分钟反应即可制得石墨烯为基底的复合材料FAG；而PVP为还原剂与AgNO3作用则得到以氧化石墨烯为基底的复合材料PAG。利用HRTEM，扫描电镜（SEM）和XPS等表征手段对PAG和FAG两种复合材料进行了研究。XPS数据显示二者的基底不同，SEM和HRTEM照片显示基底上的含氧官能团对纳米银在基底的附着有着重要的影响。这种低温且快速的制备方式为规模化生产石墨烯/纳米银复合材料开辟了新的路线。
3）为了更加方便地制备基底还原程度不一样的（氧化）石墨烯/纳米银复合材料，对2）的方法进行了改进，使用了绿色环保的试剂。加入葡萄糖，PVP和银氨溶液，通过改变反应温度制备了三种复合材料GSG-25(25oC),GSG-40(40oC)和GSG-60(60oC)，并着重研究了GSG-25和GSG-60这两种基底含氧基团差别比较大的复合材料。XPS谱图证实GSG-25和GSG-60这两种复合材料基底上含氧官能团的含量差别较大；HRTEM照片显示了纳米银在不同基底上的分布状况，对比后发现GSG-25上负载的纳米银颗粒数目更多，存在相对较多的粒径大的纳米银颗粒；利用紫外-可见光吸收(UV-vis)光谱对不同反应时间得到的复合材料进行了考察；对基底上的含氧官能团与负载的纳米银之间的相互作用进行的研究，证实了纳米银颗粒与复合材料的基底之间是非共价键的结合方式；另外，对GSG-60制备过程中的还原组分进行了讨论；最后，考察了这两种复合材料GSG-25和GSG-60在表面增强拉曼散射方面(SERS)的性能。
As a new emerging carbon materials, graphene possessed distinctmechanical, optical, thermal and electrical properties, such as anomalousquantum Hall effect, high young modulus, high thermal conductivity andhigh specific surface area. Because of these excellent properties,graphene is widely applied for the preparation of various functionalnanocomposites and which obtained applications in the field ofelectronics, optics, catalysis and so on. However, there are manyobstacles in the industrial application of graphene and large-scaleproduction of graphene is one of the main challenges. Graphene oxide(GO) is usually treated as a precursor to graphene for its structuralsimilarity with graphene. By thermal or chemical way, GO can beconverted to graphene. Especially, the routes for the modification of GOin chemical way are numberous and worthy to be investigated. The mainwork in this paper was fucosed on the surface modification of grapheneoxide and graphene (oxide) functionalized with small organic molecule orsilver nanoparticles were prepared. The main contents of the paperinclude:
1) Modification of graphene oxide with small organic molecule.2-amino-4,6-didodecylamino-1,3,5-triazine (ADDT) was firstlysynthesized from cyanuric chloride. Characterized by means of FT-IR and1HNMR, the chemical structure of ADDT was confirmed. Compared tomelamine, the thermal stability of ADDT is improved and thedecomposition temperature of ADDT matched well with that of thermoplastics. In order to modify GO by covalent bond, GO was firstlytreated by thionyl chloride and then reaction with ADDT. The obtainedproduction GO-ADDT was investigated by FT-IR, XPS and HRTEM.The results indicate that ADDT is covalently grafted onto the surface ofGO sheets by amide linkage. The thermal stability and solubility ofGO-ADDT was then discussed. According the data of TGA, the thermalstability of GO-ADDT is improved. With the increasing temperature, themass loss rate of GO-ADDT is significantly lower than that of GO. Whiledispersed in CHCl3/H2O mixture, GO-ADDT was all dispersed in CHCl3,implying the hydrophilic GO has been converted to hydrophobicGO-ADDT. And the shift will lay foundations for the application ofGO-ADDT in some nonpolar polymer-based composites.
2) Under mild conditions, graphene/silver composites was preparedby simultaneous reduction of graphene oxide and silver ions in a rapidand one-step way. In the experiment, FAG was prepared by usingformaldehyde as the reducing agent and PVP as the protect agent; WhilePAG was prepared by using PVP as reducing agent individually. The twocomposites were investigated by HRTEM, SEM and XPS. The datas fromXPS spectra show different substrates between PAG and FAG. Theimages of SEM and HRTEM indicate that the oxygen-containing groupshave an effect on the growth of silver nanocrystal. Low-temperature andshort reaction time make the approach a promising alternative for thepreparation of silver–graphene nanocomposites.
3) In order to prepared graphene (oxide)/silver composites withvarious degrees of reduction in a more convenient way, an improvingmethod is developed. By the addition of glucose,PVP and silver-ammoniasolution, GSG-25(25oC)，GSG-40(40oC) and GSG-60(60oC) areprepared under different reaction temperatures. The investigation was mainly focused on GSG-25and GSG-60. The XPS spectra confirm thecontent of oxygen-containing groups between GSG-25and GSG-60isdifferent. The distribution of silver nanoparticles on the substrates wasexhibited in HRTEM images. It is clear that there are many more silvernanoparticles on GSG-25including some particles in relatively large size.The composites under different reaction times were investigated byUV-vis spectra； The interaction between silver nanoparticles andsubstrates was investigated, and the results confirmed it is nonconvalentway; In addtion, the redox components for the preparation of GSG-60were discussed; At last, the surface enhanced raman scattering (SERS)between GSG-25and GSG-60was investigated.
1)有机小分子对氧化石墨烯的表面改性。以三聚氰氯为原料合成了有机小分子2-氨基-4，6-双十二胺-1，3，5-三嗪(ADDT)，合成产物ADDT的化学结构经傅里叶红外(FT-IR）谱和核磁共振谱1H NMR得以确定。随后对合成产物的热稳定性进行了研究，从热重分析(TGA)的结果来看，制备的ADDT相对于三聚氰胺来说具有更高的热稳定性，其分解温度范围与聚合物的分解温度范围有较大的重合。为了将ADDT以共价键的方式接枝在氧化石墨烯的表面，氧化石墨烯先与二氯亚砜反应，将表面的羧基转化为酰氯基，然后ADDT与酰氯化氧化石墨烯反应。产物GO-ADDT经FT-IR、X射线光电子能谱(XPS)和高分辨透射电镜（HRTEM）表征，确认ADDT通过酰胺键接枝在氧化石墨烯片的表面上，随后对GO-ADDT的热稳定性和溶解性进行了考察。从TGA的结果来看，接枝上ADDT之后，产物的热稳定有了明显提高，随着温度的升高其质量损失速率明显降低且GO-ADDT最后的残余量要明显高于氧化石墨。将产物GO-ADDT分散在氯仿和水的混合溶剂中，接枝后的产物表现出明显的疏水性，在氯仿中能很好的分散，这说明在改性之后，氧化石墨烯的表面由亲水转为疏水，这种变化将为GO-ADDT应用于非极性聚合物基复合材料打下基础。
2）在温和的条件下，一步法同时还原银离子和氧化石墨烯制得石墨烯/纳米银复合材料。在实验中，以甲醛为还原剂，聚乙烯吡咯烷酮(PVP)为保护剂，经过7分钟反应即可制得石墨烯为基底的复合材料FAG；而PVP为还原剂与AgNO3作用则得到以氧化石墨烯为基底的复合材料PAG。利用HRTEM，扫描电镜（SEM）和XPS等表征手段对PAG和FAG两种复合材料进行了研究。XPS数据显示二者的基底不同，SEM和HRTEM照片显示基底上的含氧官能团对纳米银在基底的附着有着重要的影响。这种低温且快速的制备方式为规模化生产石墨烯/纳米银复合材料开辟了新的路线。
3）为了更加方便地制备基底还原程度不一样的（氧化）石墨烯/纳米银复合材料，对2）的方法进行了改进，使用了绿色环保的试剂。加入葡萄糖，PVP和银氨溶液，通过改变反应温度制备了三种复合材料GSG-25(25oC),GSG-40(40oC)和GSG-60(60oC)，并着重研究了GSG-25和GSG-60这两种基底含氧基团差别比较大的复合材料。XPS谱图证实GSG-25和GSG-60这两种复合材料基底上含氧官能团的含量差别较大；HRTEM照片显示了纳米银在不同基底上的分布状况，对比后发现GSG-25上负载的纳米银颗粒数目更多，存在相对较多的粒径大的纳米银颗粒；利用紫外-可见光吸收(UV-vis)光谱对不同反应时间得到的复合材料进行了考察；对基底上的含氧官能团与负载的纳米银之间的相互作用进行的研究，证实了纳米银颗粒与复合材料的基底之间是非共价键的结合方式；另外，对GSG-60制备过程中的还原组分进行了讨论；最后，考察了这两种复合材料GSG-25和GSG-60在表面增强拉曼散射方面(SERS)的性能。
As a new emerging carbon materials, graphene possessed distinctmechanical, optical, thermal and electrical properties, such as anomalousquantum Hall effect, high young modulus, high thermal conductivity andhigh specific surface area. Because of these excellent properties,graphene is widely applied for the preparation of various functionalnanocomposites and which obtained applications in the field ofelectronics, optics, catalysis and so on. However, there are manyobstacles in the industrial application of graphene and large-scaleproduction of graphene is one of the main challenges. Graphene oxide(GO) is usually treated as a precursor to graphene for its structuralsimilarity with graphene. By thermal or chemical way, GO can beconverted to graphene. Especially, the routes for the modification of GOin chemical way are numberous and worthy to be investigated. The mainwork in this paper was fucosed on the surface modification of grapheneoxide and graphene (oxide) functionalized with small organic molecule orsilver nanoparticles were prepared. The main contents of the paperinclude:
1) Modification of graphene oxide with small organic molecule.2-amino-4,6-didodecylamino-1,3,5-triazine (ADDT) was firstlysynthesized from cyanuric chloride. Characterized by means of FT-IR and1HNMR, the chemical structure of ADDT was confirmed. Compared tomelamine, the thermal stability of ADDT is improved and thedecomposition temperature of ADDT matched well with that of thermoplastics. In order to modify GO by covalent bond, GO was firstlytreated by thionyl chloride and then reaction with ADDT. The obtainedproduction GO-ADDT was investigated by FT-IR, XPS and HRTEM.The results indicate that ADDT is covalently grafted onto the surface ofGO sheets by amide linkage. The thermal stability and solubility ofGO-ADDT was then discussed. According the data of TGA, the thermalstability of GO-ADDT is improved. With the increasing temperature, themass loss rate of GO-ADDT is significantly lower than that of GO. Whiledispersed in CHCl3/H2O mixture, GO-ADDT was all dispersed in CHCl3,implying the hydrophilic GO has been converted to hydrophobicGO-ADDT. And the shift will lay foundations for the application ofGO-ADDT in some nonpolar polymer-based composites.
2) Under mild conditions, graphene/silver composites was preparedby simultaneous reduction of graphene oxide and silver ions in a rapidand one-step way. In the experiment, FAG was prepared by usingformaldehyde as the reducing agent and PVP as the protect agent; WhilePAG was prepared by using PVP as reducing agent individually. The twocomposites were investigated by HRTEM, SEM and XPS. The datas fromXPS spectra show different substrates between PAG and FAG. Theimages of SEM and HRTEM indicate that the oxygen-containing groupshave an effect on the growth of silver nanocrystal. Low-temperature andshort reaction time make the approach a promising alternative for thepreparation of silver–graphene nanocomposites.
3) In order to prepared graphene (oxide)/silver composites withvarious degrees of reduction in a more convenient way, an improvingmethod is developed. By the addition of glucose,PVP and silver-ammoniasolution, GSG-25(25oC)，GSG-40(40oC) and GSG-60(60oC) areprepared under different reaction temperatures. The investigation was mainly focused on GSG-25and GSG-60. The XPS spectra confirm thecontent of oxygen-containing groups between GSG-25and GSG-60isdifferent. The distribution of silver nanoparticles on the substrates wasexhibited in HRTEM images. It is clear that there are many more silvernanoparticles on GSG-25including some particles in relatively large size.The composites under different reaction times were investigated byUV-vis spectra； The interaction between silver nanoparticles andsubstrates was investigated, and the results confirmed it is nonconvalentway; In addtion, the redox components for the preparation of GSG-60were discussed; At last, the surface enhanced raman scattering (SERS)between GSG-25and GSG-60was investigated.
引文
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