CN102382147B - 具有非线性光学活性的二茂铁炔基卟啉分子的制备及应用 - Google Patents
具有非线性光学活性的二茂铁炔基卟啉分子的制备及应用 Download PDFInfo
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Abstract
本发明公开了具有非线性光学活性的二茂铁炔基卟啉分子的制备方法及应用。特征是:以5,15-二溴-10,20-二苯基锌卟啉为原料在催化剂的作用下与二茂铁乙炔反应得到5,15-二茂铁炔基-10,20-二苯基锌卟啉。然后,将5,15-二茂铁炔基-10,20-二苯基锌卟啉用盐酸处理,得到5,15-二茂铁炔基-10,20-二苯基卟啉。获得的化合物具有较高的超极化率以及明显的分子内光致电子转移结构特征,并显示出反饱和吸收特性,可以应用于非线性光学和激光防护。
Description
技术领域
本发明涉及二茂铁炔基卟啉分子的制备及应用,属于有机非线性光学材料的技术领域。
背景技术
随着激光器的面世,非线性光学(nonlinear optics,NLO)也发展起来。非线性光学主要研究的是强光(如激光)与物质间的相互作用,当光达到一定的强度后,物质对光的吸收已经不再符合传统光学所给出的规律,其吸收系数会随着光强的变化而变化。由于非线性光学材料在光通讯、高速光电信息处理、高密度数据存储、短光脉冲生成、空间光调制、全光开关等领域具有潜在的巨大应用价值,因此有关非线性光学材料的研究成为当前的前沿课题之一。最早的非线性光学材料是一些诸如LiNbO3(铌酸锂)等无机晶体,但是这类无机材料往往存在非线性系数不高,无法与半导体材料集成等缺点。到了上世纪80年代中期有机材料由于具备大而超快的光学非线性,易于加工处理和集成为光学器件等突出优点而在非线性光学领域脱颖而出。与无机材料相比,有机材料的非线性光学性能可通过对材料的化学结构进行有效调节和修饰来控制,这对于实现分子水平上的微型光电信息器件的终极目标是十分理想的。同时,有机材料因其相对低廉的价格、高激光损伤阀值、快速的响应时间和较小的折射系数,在光子和生物光子器件的应用中更具优势。
当前,卟啉/酞菁分子由于具有特殊的共轭π电子结构,很好的热稳定性和化学稳定性,易于加工处理,且具有很强的非线性光学响应和超快的响应时间,正迅速成为非线性光学材料领域的研究热点。例如,富勒烯与铜酞菁通过共价键结合,所形成的给-受电子体系CuPc-C60,被证明具有很高的超极化率。
本发明提出的化合物结构上在卟啉环上通过乙炔基引入了二茂铁基团,可以形成更大的π共轭体系,且可以形成给-受电子体系。从结构上可以推测具有很高的超极化率,将具有良好的非线性光学活性。
发明内容
本发明的目的之一是具有非线性光学活性的二茂铁炔基卟啉分子,该化合物具有以下结构:
本发明的目的之二是推出该化合物的制备方法。本发明采用以下技术方案实现以上目的:
(1)将5,15-二溴-10,20-二苯基锌卟啉和二茂铁乙炔溶于四氢呋喃中,搅拌加入二(三苯基膦)二氯化钯,碘化亚铜,乙二胺,在55~65℃下反应10~12小时,反应结束后,将溶剂减压除去,在硅胶柱上用纯氯仿淋洗进行提纯,氯仿和甲醇重结晶得到5,15-二茂铁炔基-10,20-二苯基锌卟啉;其中5,15-二溴-10,20-二苯基锌卟啉和二茂铁乙炔的摩尔比为1∶3~1∶4;
(2)将5,15-二茂铁炔基-10,20-二苯基锌卟啉溶于氯仿中,加入盐酸搅拌0.5~1小时,然后用蒸馏水洗涤,分液,干燥,将溶剂减压除去后得到目标产物5,15-二茂铁炔基-10,20-二苯基卟啉。
所述步骤(1)中二(三苯基膦)二氯化钯加入量为反应物总量的3%~5%,碘化亚铜加入量为反应物总量的0.5%~1%。
所述步骤(2)中氯仿与盐酸的体积为3∶1~5∶1,盐酸浓度为6mol/L。
合成路线如下所示:
本发明的目的之三是提供二茂铁炔基卟啉分子的应用。该化合物具有较高的超极化率以及明显的分子内光致电子转移结构特征,并显示出反饱和吸收特性,可以应用于非线性光学和激光防护。本发明涉及化合物的非线性光学活性通过Z-扫描技术测试,结果见附图1、2。从附图1可以看出,随着入射光强的增强,归一化透过率随着入射光强的增大而变小,在焦点附近最小(谷),呈现反饱和吸收现象。计算样品的非线性极化率χ(3)为2.442×10-12esu。紫外吸收光谱图(附图3)显示该类材料的最大吸收波长为436nm。
与背景技术相比,本发明具有以下优点:
(1)本发明由5,15-溴代-10,20-二苯基锌卟啉出发,经过取代和水解反应首次制备新型卟啉分子5,15-二茂铁炔基-10,20-二苯基卟啉。制备的5,15-二茂铁炔基-10,20-二苯基卟啉分子利用核磁共振谱、质谱以及紫外吸收光谱图进行了表征,确证了分子结构。
本发明在合成步骤(1)中加入的二(三苯基膦)二氯化钯和碘化亚铜有效提高了取代反应的产率。与背景技术相比,其制备方法工艺简单,条件温和,易操作。
(2)二茂铁炔基取代卟啉分子具有较高的超极化率以及明显的分子内光致电子转移结构特征,并显示出反饱和吸收特性。可以用于激光防护、全光开关,光存储等领域。
附图说明
图1本发明的开孔Z-扫描图。
图2本发明的Z-扫描纯折射的归一化透过率曲线图。
图3本发明的紫外吸收光谱图。
具体实施方式
现结合实施例进一步说明本发明的技术方案。
实施例1
5,15-二茂铁炔基-10,20-二苯基卟啉的制备
(1)将5,15-二溴-10,20-二苯基锌卟啉(305mg,0.45mmol)和二茂铁乙炔(284mg,1.35mmol)溶于四氢呋喃(10ml)中,搅拌加入二(三苯基膦)二氯化钯Pd(PPh3)2Cl2(30mg,0.04mmol),碘化亚铜CuI(3mg,0.02mmol),乙二胺(2ml),在65℃下反应10小时,反应结束后,将溶剂减压除去,在硅胶柱上用纯氯仿淋洗进行提纯,氯仿和甲醇重结晶得到5,15-二茂铁炔基-10,20-二苯基锌卟啉,产率60%。
(2)将5,15-二茂铁炔基-10,20-二苯基锌卟啉(200mg,0.12mmol)溶于20mL氯仿中,加入5mL盐酸搅拌1h,然后用蒸馏水洗涤,分液,干燥,将溶剂减压除去后得到目标产物5,15-二茂铁炔基-10,20-二苯基卟啉,产率65%。核磁共振谱(CDCl3,300MHz):δ9.62(d,4H,Por βH),8.83(d,4H,Por βH),8.21(d,4H,Ph H),7.80(s,6H,Ph H),4.95(m,4H,Fc H),4.13(m,14H,Fc H),-1.86(s,2H,PorN H).质谱:C56H38N4Fe2[M+H]+计算值为879.3,实测值为878.7。
实施例2
5,15-二茂铁炔基-10,20-二苯基卟啉的制备
(1)将5,15-二溴-10,20-二苯基锌卟啉(305mg,0.45mmol)和二茂铁乙炔(378mg,1.80mmol)溶于四氢呋喃(10ml)中,搅拌加入二(三苯基膦)二氯化钯Pd(PPh3)2Cl2(20mg,0.03mmol),碘化亚铜CuI(6mg,0.04mmol),乙二胺(2ml),在55℃下反应12小时,反应结束后,将溶剂减压除去,在硅胶柱上用纯氯仿淋洗进行提纯,氯仿和甲醇重结晶得到5,15-二茂铁炔基-10,20-二苯基锌卟啉,产率52%。
(2)将5,15-二茂铁炔基-10,20-二苯基锌卟啉(200mg,0.12mmol)溶于20mL氯仿中,加入7mL盐酸搅拌0.5h,然后用蒸馏水洗涤,分液,干燥,将溶剂减压除去后得到目标产物5,15-二茂铁炔基-10,20-二苯基卟啉,产率70%。核磁共振谱(CDCl3,300MHz):δ9.62(d,4H,Por βH),8.83(d,4H,Por βH),8.21(d,4H,Ph H),7.80(s,6H,Ph H),4.95(m,4H,Fc H),4.13(m,14H,Fc H),-1.86(s,2H,Por N H).质谱:C56H38N4Fe2[M+H]+计算值为879.3,实测值为878.7。
实施例3
5,15-二茂铁炔基-10,20-二苯基卟啉三阶非线性性质的测定
利用Z扫描技术测量了5,15-二茂铁炔基-10,20-二苯基卟啉的非线性吸收和非线性折射,测量在纯氯仿中进行,化合物的浓度为10-4mol/L-1。实验中装样品的比色皿厚度为1mm,透镜焦点处束腰半径w0为40μm,小孔的线性透过率S为0.1,在透镜焦点处光功率密度为7.593×109W/cm2。在测量之前,用二硫化碳对整个体系进行校准。我们在同样的条件下对纯溶剂CHCl3进行了测量,以确定测得的曲线均起源于化合物的性质而不受溶剂的影响。
Claims (3)
1.具有非线性光学活性的二茂铁炔基卟啉分子,其特征在于分子具有以下结构:
2.权利要求1所述的二茂铁炔基卟啉分子的制备方法,其特征在于,该方法包含以下步骤:
(1)将5,15-二溴-10,20-二苯基锌卟啉和二茂铁乙炔溶于四氢呋喃中,搅拌加入二(三苯基膦)二氯化钯,碘化亚铜,乙二胺,在55~65℃下反应10~12小时,反应结束后,将溶剂减压除去,在硅胶柱上用纯氯仿淋洗进行提纯,氯仿和甲醇重结晶得到5,15-二茂铁炔基-10,20-二苯基锌卟啉;其中5,15-二溴-10,20-二苯基锌卟啉和二茂铁乙炔的摩尔比为1∶3~1∶4;
(2)将5,15-二茂铁炔基-10,20-二苯基锌卟啉溶于氯仿中,加入盐酸搅拌0.5~1小时,然后用蒸馏水洗涤,分液,干燥,将溶剂减压除去后得到目标产物5,15-二茂铁炔基-10,20-二苯基卟啉;
其中,所述步骤(1)中二(三苯基膦)二氯化钯加入量为反应物总量的3%~5%,碘化亚铜加入量为反应物总量的0.5%~1%;
所述步骤(2)中氯仿与盐酸的体积为3∶1~5∶1,盐酸浓度为6mol/L。
3.权利要求1所述的二茂铁炔基卟啉分子在非线性光学和激光防护中的应用。
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