CN114773363B - 一种光控荧光变色材料及其制备方法和应用 - Google Patents
一种光控荧光变色材料及其制备方法和应用 Download PDFInfo
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Abstract
本发明公开了一种光控荧光变色材料及其制备方法和应用,其中光控荧光变色材料为配合物1—[(C12H11N2)2(C8H3NO6)2(H2O)2Zn]n或配合物2——[(C24H22N4)(C8H3NO6)2(H2O)2Zn]n。配合物1在365nm紫外光的辐射下,平行的两个烯键发生[2+2]环加成反应,转变成配合物2—[(C24H22N4)(C8H3NO6)2(H2O)2Zn]n。本发明中,由于配合物晶体内部两个平行且紧密排列的1,2‑(3‑吡啶基)‑(4‑吡啶基)‑乙烯阳离子发生环加成反应,生成环丁烷衍生物,导致吡啶配体的共轭性发生改变,从而影响了配合物的荧光发光性能。
Description
技术领域
本发明属于荧光材料技术领域,确切地说是一种光控荧光变色材料及其制备方法和应用。
背景技术
以洁净、节能和节约为目标的光化学合成反应是化学、材料、能源、环境等多个学科共同关注的新兴领域,为新材料的制备提供了新方法和新技术。光化学合成反应是指在光的作用下进行新化合物或功能材料的合成研究。通常用紫外光或可见光,使电子从基态跃迁到激发态,然后这一激发态再进行其它光物理和光化学过程。光化学合成反应可以在固相、液相或气相下发生。其中,固相光化学合成尤其引人注目,特别是在晶体状态下,光照直接得到新物质的研究具有非常重要的理论意义和实用价值。
根据Schmidt提出的烯烃光环加成反应的理论:相邻烯烃分子中的烯键须平行排列,且相邻烯键的距离范围在烯烃才能够表现出光反应活性。然而,在自然状态下结晶的纯烯烃化合物分子往往无法形成其发生光环加成反应的堆积模式。利用配位键可以使分子和离子定向排列,从而形成具有特定结构和功能的配位聚合物。通过配位键的模板作用,能够使烯烃配体中的烯键平行排列,并拉近它们之间的距离。因此,配位化合物可作为研究烯烃[2+2]光环加成反应的载体。近年来,科学家利用光敏有机分子的光化学反应开发了系列基于光化学反应的光控荧光材料,这些材料在光信息储存、光学传感器等方面具有明确的应用前景。
发明内容
本发明提供了一种光控荧光变色材料及其制备方法和应用。本发明光控荧光变色材料配合物1的荧光最大发射波长为486nm,为蓝绿光;配合物2的荧光最大发射波长为431nm,为蓝光。荧光的最大发射波长蓝移了55nm。本发明光控荧光变色材料,合成步骤简单,产率高,能够大量制备。
本发明光控荧光变色材料,为配合物1——[(C12H11N2)2(C8H3NO6)2(H2O)2Zn]n或配合物 2——[(C24H22N4)(C8H3NO6)2(H2O)2Zn]n。
配合物1的晶体属于三斜晶系,空间群为Pī,晶胞参数为 α=113.81(3)°,β=100.81(3)°,γ=93.87(3)°;
配合物2的晶体属于三斜晶系,空间群为Pī,晶胞参数为 α=112.14(3)°,β=101.03(3)°,γ=94.19(3)°。
配合物1在365nm紫外光的辐射下,平行的两个烯键发生[2+2]环加成反应,转变成配合物2——[(C24H22N4)(C8H3NO6)2(H2O)2Zn]n。本发明中,由于配合物晶体内部两个平行且紧密排列的1,2-(3-吡啶基)-(4-吡啶基)-乙烯阳离子发生环加成反应,生成环丁烷衍生物,导致吡啶配体的共轭性发生改变,从而影响了配合物的荧光发光性能。配合物1的荧光最大发射波长为486nm,为蓝绿光;配合物2的荧光最大发射波长为431nm,为蓝光。配合物2的荧光最大发射波长较配合物1蓝移了55nm。
本发明光控荧光变色材料的制备方法,包括如下步骤:
步骤1:配合物1的合成
将1-(3-吡啶基)-2-(4-吡啶基)-乙烯、2-硝基-1,4-苯二甲酸、六水合硝酸锌和去离子水置于反应釜中,于170℃恒温反应48小时,反应结束后缓慢冷却至室温,过滤、洗涤、收集晶态化合物,可得配合物1——[(C12H11N2)2(C8H3NO6)2(H2O)2Zn]n;
步骤2:由配合物1转变为配合物2
将配合物1晶体置于发射波长为365nm的LED紫外灯下5cm距离处,光照30分钟,即可得到配合物2——[(C24H22N4)(C8H3NO6)2(H2O)2Zn]n。
本发明配合物1中,相邻的两个1-(3-吡啶基)-2-(4-吡啶基)-乙烯中的烯键,在365nm的LED紫外灯辐射下,转变为环丁烷衍生物的结构示意:
根据Schmidt[2+2]光环加成反应理论,即相邻烯键平行,并且双键间的距离小于在配合物1中,烯键平行且双键间的距离为/>配合物1完全转化为配合物2,其收率为100%。
在385nm波长光的激发下,配合物1的荧光最大发射波长为486nm,为蓝绿光;在385nm 波长光的激发下,配合物2的荧光最大发射波长为431nm,为蓝光。配合物2较配合物1的荧光最大发射波长蓝移了55nm。
本发明制备方法工艺简单、反应条件温和、产率高。
附图说明
图1为配合物1——[(C12H11N2)2(C8H3NO6)2(H2O)2Zn]n的晶体结构图。配合物1的结构特点为,相邻烯键平行排列,且烯键间的距离(虚线表示)为
图2为配合物2——[(C24H22N4)(C8H3NO6)2(H2O)2Zn]n的晶体结构图。配合物2的结构特点为,相邻的烯键发生[2+2]环加成反应,生成环丁烷衍生物。
图3为配合物1和配合物2的荧光发射光谱图。
具体实施方式
非限定实施例叙述为下:
1-(3-吡啶基)-2-(4-吡啶基)-乙烯根据Alvaro Gordillo等人发表的文章Mechanistic Studies on the Pd-Catalyzed Vinylation of Aryl Halides withVinylalkoxysilanes in Water:The Effect of the Solvent and NaOH Promoter方法合成(参见:Alvaro Gordillo,Manuel A.Ortuno,Carmen Lopez-Mardomingo,AgustíLledos,GregoriUjaque,Ernesto de Jesus,J.Am.Chem.Soc.,2013,135, 13749–13763)。2-硝基-1,4-苯二甲酸和六水合硝酸锌从国药集团化学试剂有限公司购置。
1、配合物1——[(C12H11N2)2(C8H3NO6)2(H2O)2Zn]n的制备
将1-(3-吡啶基)-2-(4-吡啶基)-乙烯0.91g(5mmol),2-硝基-1,4-苯二甲酸1.05g(5mmol),六水合硝酸锌1.49g(5mmol)和去离子水(20mL)加入到40mL反应釜中,将反应釜密封并置于170℃恒温反应48小时,反应结束后缓慢冷却至室温,得到无色晶体,过滤、洗涤、收集晶态化合物,室温下晾干,可得配合物1,产量:3.10g,产率:70%。其晶体学参数如下:
配位聚合物1的晶体学参数:C40H32N6O14Zn,Mr=886.11,triclinic,space group Pī, α=113.81(3)°,β=100.81(3)°,γ=93.87(3)°,/> Z=1,Dc=1.560g cm-3,μ=0.733mm-1,17428reflectionsmeasured,4307unique reflections(Rint=0.0316),3784observed reflections(I>2σ(I)),281parameters,R1=0.0329,wR2= 0.0720,S=1.051。
配合物1的X-射线单晶结构图见图1。
2、由配合物1转变为配合物2——[(C24H22N4)(C8H3NO6)2(H2O)2Zn]n
将配合物1(0.31g,0.5mmol)置于直径为10cm的培养皿内,然后放置于发光波长为365nm的LED紫外灯(20W)下5cm距离处光照30分钟,即可得到配合物2,产量:0.31g,产率:100%。其晶体学参数如下:
配位聚合物2的晶体学参数:C40H32N6O14Zn,Mr=886.11,triclinic,space group Pī, α=112.14(3)°,β=101.03(3)°,γ=94.19(3)°,/> Z=1,Dc=1.552g cm-3,μ=0.729mm-1,16768reflectionsmeasured,4344unique reflections(Rint=0.0361),3452observed reflections(I>2σ(I)),277parameters,R1=0.0402,wR2= 0.0783,S=1.095。
配合物2的X-射线单晶结构图见图2。
3、配合物1和配合物2的荧光性质
配合物1和2都展现出良好的荧光性质。配合物1和2的固体荧光发射光谱均在室温条件下测定(图3)。配合物1和2在波长为385nm光的激发下发射荧光,其最大发射波长分别为486nm (1)和431nm(2),而羧酸配体2-硝基对苯二甲酸在上述波长光的激发下没有荧光。已知1-(3- 吡啶基)-2-(4-吡啶基)-乙烯的最大发射波长为428nm(λex=370nm),配合物1的最大发射波长相对于1-(3-吡啶基)-2-(4-吡啶基)-乙烯配体发生了略微红移,它们的荧光源于配体的π-π*跃迁。而相对于配合物1,配合物2的荧光最大发射波长发生了明显蓝移,蓝移了55nm。这可能是因为新形成的1,3-双(3-吡啶基)-2,4-双(4-吡啶基)-环丁烷配体与中心Zn(II)原子之间发生电子转移导致的。
配合物1和2的荧光发射光谱见图3。
Claims (2)
1.一种光控荧光变色材料,其特征在于:
所述光控荧光变色材料为配合物1——[(C12H11N2)2(C8H3NO6)2(H2O)2Zn] n 或配合物2——[(C24H22N4)(C8H3NO6)2(H2O)2Zn] n ;n为重复单元数,是任意正整数;
所述配合物1的晶体属于三斜晶系,空间群为Pī,晶胞参数为a = 7.7103(15) Å,b =10.635(2) Å,c = 12.967(3)Å,α= 113.81(3)˚,β = 100.81(3)˚,γ = 93.87(3)˚;
所述配合物2的晶体属于三斜晶系,空间群为Pī,晶胞参数为a = 7.9714(16) Å,b =11.008(2) Å,c = 12.039(2) Å,α= 112.14(3)˚,β = 101.03(3)˚,γ = 94.19(3)˚。
2.一种权利要求1所述的光控荧光变色材料的制备方法,其特征在于包括如下步骤:
步骤1:配合物1的合成
将1-(3-吡啶基)-2-(4-吡啶基)-乙烯、2-硝基-1,4-苯二甲酸、六水合硝酸锌和去离子水置于反应釜中,于170℃恒温反应48小时,反应结束后缓慢冷却至室温,过滤、洗涤、收集晶态化合物,可得配合物1——[(C12H11N2)2(C8H3NO6)2(H2O)2Zn] n ;
步骤2:配合物2的合成
将配合物1晶体置于发光波长为365 nm的LED紫外灯下5 cm距离处,光照30分钟,即可得到配合物2——[(C24H22N4)(C8H3NO6)2(H2O)2Zn] n 。
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