以4-氨基硝基苯为原料,通过溴代、重氮化去氨基、硝基还原和重氮偶合反应合成了3',5'-二溴-3-甲氧基-4-羟基偶氮苯,并通过物理掺杂方法制备了3',5'-二溴-3-甲氧基-4-羟基偶氮苯-聚甲基丙烯酸甲酯(PMMA)薄膜.利用元素分析、红外光谱、质谱、核磁共振和X射线单晶衍射等技术手段对标题化合物结构进行了表征.晶体结构分析表明,标题化合物晶体属于单斜晶系,C2/c空间群,晶胞参数为a=1.6182(3) nm,b =0.81847(16) nm,c=2.1945(4) nm,β=102.819(2)°,V=2.8342(10) nm3,Z =8,Dc =1.809 g/cm3,μ=5.719 mm-1,F(000)=1504,R1=0.0366,ωR2=0.0764,化合物分子呈反式平面构型,分子间存在的氢键和苯环,π-π堆积作用使得其沿b轴方向形成了一维无限链状结构.用紫外-可见光谱对标题化合物在有机溶剂、聚合物中光致反-顺异构化反应和热回复异构化反应的速率常数进行了定量测试,异构化反应的速率常数的数量级为10-1～ 10-2 min-1.
参考文献
| [1] | Yamada M;Kondo M;Mamiya J.Photomobile Polymer Materials:Towards Light-driven Plastic Motors[J].Angew Chem Int Ed Engl,200847(27):4986-4988. |
| [2] | Muraoka T;Kinbara K;Kobayashi Y.Light-driven Open-close Motion oο Fhiral Molecular Scissors[J].Journal of the American Chemical Society,2003125(19):5612-5613. |
| [3] | Wen Y Q;Yi W H;Meng L J.Photochemical-controlled Switching Based on Azobenzene Monolayer Modified Silicon[J].Journal of Physical Chemistry B,2005109(30):14465-14468. |
| [4] | Dhammika B H M;Friss T R;Enriquez M M.Proof for the Concerted Inversion Mechanism in the trans-cis Isomerization of Azobenzene Using Hydrogen Bonding to Induce Isomer Locking[J].Journal of Organic Chemistry,201075(14):4817-4827. |
| [5] | Russew M M;Hecht S.Photoswitches:from Molecules to Materials[J].Advanced Materials,201022(31):3348-3360. |
| [6] | Takaishi K;Muranaka A;Kawamoto M.Photoinversion of Cisoid/transoid Binaphthyls[J].Organic Letters,201214(01):276-279. |
| [7] | Wang X L;Huang J;Zhou Y Y.Conformational Switching of G-Quadruplex DNA by Photoregulation[J].Angew Chem Int Edn Engl,201049(31):5305-5309. |
| [8] | Yu G C;Han C Y;Zhang Z B.Pillar[6]arene-based Photoresponsive Host-guest Complexation[J].Journal of the American Chemical Society,2012134(20):8711-8717. |
| [9] | Gao J;He Y N;Liu F.Azobenzene Supramolecular Side-chain Polymer Films for Laser-induced Surface Relief Gratings[J].CHEMISTRY OF MATERIALS,200719(16):3877-3881. |
| [10] | Gao J;He Y N;Xu H P.Azobenzene-containing Supramolecular Polymer Films for Laser-induced Surface Relief Gratings (111) Surface[J].CHEMISTRY OF MATERIALS,200719(01):14-17. |
| [11] | Ichimura K.Photoaligument of Liquid-crystal System[J].CHEMICAL REVIEWS,2000100(05):1847-1873. |
| [12] | Yamada M;Kondo M;Miyasato R.Photoresponsive Behavior of Laminated Films Composed of a Flexible Plastic Sheet and a Crosslinked Azobenzene Liquid-crystalline Polymer Layer with Different Initial Alignment of Mesogens[J].Molecular Crystals and Liquid Crystals,2009498(01):65-73. |
| [13] | 王辉 .取代偶氮苯化合物的合成及其光致变色性能的研究[D].武汉:华中师范大学,2004. |
| [14] | 赵宇飞 .偶氮苯化合物的合成及光致变色性能的研究[D].北京:北京化工大学,2009. |
| [15] | 罗洋城 .基于光致双折射效应的有机聚合物薄膜全光开关效应研究[D].广州:中山大学,2005. |
| [16] | Stephanie H;James M T.Synthesis of Anthropomorphic Molecules:The NanoPutians[J].Journal of Organic Chemistry,200368(23):8750-8766. |
| [17] | 陈小明;蔡继文.单晶结构分析的原理与实践[M].北京:科学出版社,2007:125. |
| [18] | 王艳;张其震.含硝基二代光致变色液晶树枝状大分子的光化学研究[J].化学学报,200664(15):1593-1600. |
| [19] | Conti I;Marchioni F;Credi A.Cyclohexenylphenyldiazene:A Simple Surrogate of the Azobenzene Photochromic Unit[J].Journal of the American Chemical Society,2007129(11):3198-3210. |
| [20] | 张其震;张静智;王艳.含偶氮苯基侧基聚硅氧烷的合成及光致变色性[J].高分子学报,1996(01):121-125. |
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