CN102703984A - 一种有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸及其制备方法 - Google Patents
一种有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸及其制备方法 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及一种有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸及其制备方法。
背景技术
随着20世纪末全球信息化浪潮的迅猛发展和光电子技术的广泛应用,国内外对光电功能晶体尤其是二阶非线性光学晶体的需求量剧增。二阶非线性光学晶体材料广泛用于激光及光通讯领域,其研究已成为高科技领域重要的研究课题之一。迄今为止,无机二阶非线性光学晶体无论在学术研究还是在产业化方面都取得了重大成果,但随着光电信息产业的迅速发展,对高速高密度数据处理要求的提高使得传统的无机晶体材料难以完全满足需要。因此,迫切需要开发具有大非线性系数和高电光性能的新材料-有机二阶非线性光学材料。有机二阶非线性光学材料与无机二阶非线性光学材料相比,突出的优点是:(1)有机材料的光极化来源于高度离域的π电子的极化,其极化比无机材料的离子极化容易,导致其非线性系数比无机材料高1-2个数量级;(2)相应速度快,接近于飞秒;(3)光学损伤阈值高;(4)可通过分子设计优化分子性能;(5)可通过聚集态控制材料的性能。设计二阶非线性光学材料的关键是如何诱导无心结构的形成及如何增加化合物的极化率,因此,在有机二阶非线性光学材料的设计合成中,不仅要求有机分子具有非中心对称的结构,关键其聚集态也要具有非中心对称的结构,即其晶体结构是非中心对称的。按照这一设计思路,我们设计并制备了一种具有非中心对称结构的新型二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸。
发明内容
本发明的目的在于提供一种有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸及其制备方法,其合成方法简单、易操作、原料来源充足、生产成本低廉、化合物晶体合成的产率及纯度高,重复性好,使得其适合扩大化生产的要求,该有机化合物晶体的倍频效应为KDP(磷酸二氢钾)的2.5倍,可以作为一种潜在的有机二阶非线性光学材料。
本发明是这样来实现的,一种有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸,其特征是化学式为C9H7N3O2,单斜晶系,空间群为Pn,单胞参数为 α=90°,β=93~96°,γ=90°,Z=2。
所述的有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸的制备方法,其特征是将1,2,4-1H-三氮唑和碳酸钾按摩尔比1∶1及10毫升N,N′-二甲基甲酰胺为溶剂混合加入圆底烧瓶中,并在磁力搅拌条件加入0.2毫升氯化三辛基甲基胺作相转移催化剂,加热至90摄氏度,5分钟后,逐滴加入对氟苯甲醛,对氟苯甲醛与1,2,4-1H-三氮唑的摩尔比为1∶1,反应24小时,生成大量黄色沉淀;将反应液冷却后加入冰中,稍加搅拌后在冰箱中静置冷却30分钟,析出沉淀,抽滤,用乙醚淋洗,烘干得到4-((1,2,4-三氮唑)-1-基)苯甲醛。
所述的有机二阶非线性光学晶体4-((1,2,4-三氮唑)-1-基)苯甲酸晶体的培养方法,其特征是将合成的4-((1,2,4-三氮唑)-1-基)苯甲醛和硝酸银按摩尔比1∶2加入圆底烧瓶中,再加入60毫升质量百分比为7%的氢氧化钠溶液;反应在60摄氏度油浴条件下磁力搅拌24小时,冷却后抽滤,在滤液中逐滴滴加质量百分比为36%~38%浓盐酸酸化,调节pH至2~3后有大量淡黄沉淀,抽 滤,用乙醚淋洗后干燥,得到淡黄色固体,然后用N,N′-二甲基甲酰胺重结晶得无色块状晶体。结晶得无色块状4-((1,2,4-三氮唑)-1-基)苯甲酸晶体,产率约为65%。
所述的有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸的应用,其特征是其倍频效应为KDP(磷酸二氢钾)的2.5倍,可作为二阶非线性光学材料。
本发明所述的4-((1,2,4-三氮唑)-1-基)苯甲酸,其特征是应用于二阶非线性光学晶体材料。
本发明具体反应式为:
②C9H7N3O(4-((1,2,4-三氮唑)-1-基)苯甲醛)+AgNO3(硝酸银)+2NaOH(氢氧化钠)→C9H6N3O2Na(4-((1,2,4-三氮唑)-1-基)苯甲酸钠)+Ag(银)+NaNO3(硝酸钠)+H2O(水)
③C9H6N3O2Na(4-((1,2,4-三氮唑)-1-基)苯甲酸钠)+HCl(盐酸)→C9H7N3O2(4-((1,2,4-三氮唑)-1-基)苯甲酸)+NaCl(氯化钠)
本发明的优点是:1、得到的有机化合物具有良好的二阶非线性光学特性,其倍频效应是商业应用广泛的无机二阶非线性光学晶体材料磷酸二氢钾(简称KDP)的2.5倍;2、合成方法简单,易操作、原料来源充足、生产成本低廉、化合物合成的产率较高,纯度也很高以及重复性好,使得其适合扩大化生产的要求。
附图说明
图1为本发明有机化合物分子通过分子间的氢键作用形成的一维链结构。
具体实施方式
本发明的化合物4-((1,2,4-三氮唑)-1-基)苯甲酸的合成:
4-((1,2,4-三氮唑)-1-基)苯甲酸是通过三步反应得到的,具体反应式为:
②C9H7N3O(4-((1,2,4-三氮唑)-1-基)苯甲醛)+AgNO3(硝酸银)+2NaOH(氢氧化钠)→C9H6N3O2Na(4-((1,2,4-三氮唑)-1-基)苯甲酸钠)+Ag(银)+NaNO3(硝酸钠)+H2O(水)
③C9H6N3O2Na(4-((1,2,4-三氮唑)-1-基)苯甲酸钠)+HCl(盐酸)→C9H7N3O2(4-((1,2,4-三氮唑)-1-基)苯甲酸)+NaCl(氯化钠)
具体操作步骤为:将1,2,4-1H-三氮唑(0.033摩尔)、碳酸钾(0.033摩尔)及N,N′-二甲基甲酰胺(10毫升)混合加入圆底烧瓶中,并在磁力搅拌条件加入0.2毫升氯化三辛基甲基胺作相转移催化剂,加热至90摄氏度,5分钟后,逐滴加入对氟苯甲醛(与1,2,4-1H-三氮唑的摩尔比为1∶1),反应24小时,生成大量黄色沉淀。将反应液冷却后加入至50毫升冰中,稍加搅拌后在冰箱中静置冷却30分钟,析出沉淀,抽滤,用少量乙醚淋洗,烘干。将合成的4-((1,2,4-三氮唑)-1-基)苯甲醛(0.01摩尔)和硝酸银(0.02摩尔)加入圆底烧瓶中,再加入60毫升质量百分比为7%的氢氧化钠(NaOH)溶液。反应在60摄氏度油浴条件下磁力搅拌24小时。冷却后抽滤。在滤液中逐滴滴加60毫升质量百分比为酸化,调节pH至2~3后有大量淡黄色沉淀,抽滤,用乙醚淋洗后干燥,得到淡黄色固体,然后用N,N′-二甲基甲酰胺重结晶得无色块状4-((1,2,4-三氮唑)-1-基)苯甲酸晶体,产率约为65%。经单晶衍射仪和元素分析测试表明该晶体为目标有机化合物。氢核磁谱分析结果为:1H-NMR(400MHz,DMSO-d6(氘 代二甲基亚砜),δ,ppm):13.10(s,1H),9.41(s,1H),8.29(s,1H),8.12(d,2H),and8.02(d,2H);元素分析测试结果为:计算值(分析值)(%):C,57.14(57.10);H,3.70(3.73);N,22.20(22.25)。
Claims (4)
1.一种有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸,其特征是化学式为C9H7N3O2,单斜晶系,空间群为Pn,单胞参数为 α=90°,β=93~96°,γ=90°,Z=2。
2.一种权利要求1所述的有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸的制备方法,其特征是将1,2,4-1H-三氮唑和碳酸钾按摩尔比1∶1及10毫升N,N′-二甲基甲酰胺为溶剂混合加入圆底烧瓶中,并在磁力搅拌条件加入0.2毫升氯化三辛基甲基胺作相转移催化剂,加热至90摄氏度,5分钟后,逐滴加入对氟苯甲醛,对氟苯甲醛与1,2,4-1H-三氮唑的摩尔比为1∶1,反应24小时,生成大量黄色沉淀;将反应液冷却后加入冰中,稍加搅拌后在冰箱中静置冷却30分钟,析出沉淀,抽滤,用乙醚淋洗,烘干得到4-((1,2,4-三氮唑)-1-基)苯甲醛。
3.一种权利要求1所述的有机二阶非线性光学晶体4-((1,2,4-三氮唑)-1-基)苯甲酸晶体的培养方法,其特征是将合成的4-((1,2,4-三氮唑)-1-基)苯甲醛和硝酸银按摩尔比1∶2加入圆底烧瓶中,再加入60毫升质量百分比为7%的氢氧化钠溶液;反应在60摄氏度油浴条件下磁力搅拌24小时,冷却后抽滤,在滤液中逐滴滴加质量百分比为36%~38%浓盐酸酸化,调节pH至2~3后有大量淡黄沉淀,抽滤,用乙醚淋洗后干燥,得到淡黄色固体,然后用N,N′-二甲基甲酰胺重结晶得无色块状晶体。
4.一种权利要求1所述的有机二阶非线性光学晶体材料4-((1,2,4-三氮唑)-1-基)苯甲酸的应用,其特征是其倍频效应为KDP(磷酸二氢钾)的2.5倍,可作为二阶非线性光学材料。
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CN104862783A (zh) * | 2015-06-09 | 2015-08-26 | 中国科学院理化技术研究所 | 一种c23h15no2非线性光学晶体及其制法和用途 |
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CN103388181A (zh) * | 2013-07-08 | 2013-11-13 | 中国科学院福建物质结构研究所 | 太赫兹非线性光学晶体4-(4-二甲基氨基苯乙烯基)甲基吡啶·对氯苯磺酸盐 |
CN104862783A (zh) * | 2015-06-09 | 2015-08-26 | 中国科学院理化技术研究所 | 一种c23h15no2非线性光学晶体及其制法和用途 |
CN104862783B (zh) * | 2015-06-09 | 2017-11-21 | 中国科学院理化技术研究所 | 一种c23h15no2非线性光学晶体及其制法和用途 |
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