CN106946736B - 芘-肼基苯甲酸及其制备方法和应用 - Google Patents
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- 238000002360 preparation method Methods 0.000 title abstract description 6
- 230000003287 optical effect Effects 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- KFGVDCBVGNMCJC-UHFFFAOYSA-N 2-hydrazinylbenzoic acid Chemical compound NNC1=CC=CC=C1C(O)=O KFGVDCBVGNMCJC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229960000583 acetic acid Drugs 0.000 claims abstract description 5
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 239000012043 crude product Substances 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims abstract description 3
- 229940125904 compound 1 Drugs 0.000 claims description 17
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- 235000019441 ethanol Nutrition 0.000 claims description 4
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 abstract description 10
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 abstract description 6
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- 238000010521 absorption reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 239000003480 eluent Substances 0.000 description 4
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- 229910002027 silica gel Inorganic materials 0.000 description 2
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- VBYDSMBICNUTKN-UHFFFAOYSA-N 3-hydrazinylbenzoic acid Chemical compound NNC1=CC=CC(C(O)=O)=C1 VBYDSMBICNUTKN-UHFFFAOYSA-N 0.000 description 1
- PCNFLKVWBDNNOW-UHFFFAOYSA-N 4-hydrazinylbenzoic acid Chemical compound NNC1=CC=C(C(O)=O)C=C1 PCNFLKVWBDNNOW-UHFFFAOYSA-N 0.000 description 1
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
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Abstract
本发明属于三阶非线性光学材料领域，公开一种芘‑肼基苯甲酸及其制备方法和应用。其通式如下：；其中，R1~R5中至少一个、至多三个为羧基，其它则为H。将1‑芘甲醛溶解在无水乙醇中，再加入肼基苯甲酸和冰乙酸，搅拌，加热回流反应，TLC跟踪反应，直到1‑芘甲醛反应完为止，蒸发溶剂，获得粗品，再经纯化，即得目标产品。本发明所述芘‑肼基苯甲酸合成条件温和，步骤简单，易于提纯，为设计合成其他具有三阶非线性的芘‑肼基酸类化合物提供了参考。此外，本发明中的两个化合物通过飞秒激光Z扫描测试，结果表明化合物有很好的三阶非线性，在三阶非线性光学材料方面具有潜在的应用价值。
Description
技术领域
本发明属于三阶非线性光学材料领域，具体涉及芘-肼基苯甲酸及其制备方法和应用。
背景技术
三阶非线性光学效应是指材料与强光作用后，由于出现非线性极化而产生的各种光学物理现象。三阶非线性光学材料是重要的光电信息功能材料，在图像处理、光学储存和记忆系统等领域有较大的应用潜力。随着光电信息产业的迅速发展，设计三阶非线性光学特性强而响应速度极快的新型材料成为人类主要研究的课题之一 。与传统的无机光学非线性材料相比，有机三阶非线性光学材料具有激光损伤阈值高、介电常数低等特点而倍受到人们的关注。
发明内容
本发明的目的在于提供一种芘-肼基苯甲酸及其制备方法和应用。
为实现上述目的，本发明采取的技术方案如下：
芘-肼基苯甲酸，其通式如下：
；其中，R1~R5中至少一个、至多三个为羧基，其它则为H。
较好地，所述芘-肼基苯甲酸为化合物1或化合物2，化合物1~2的结构式分别为：
、。
制备方法：将1-芘甲醛溶解在无水乙醇中，再加入肼基苯甲酸和冰乙酸，搅拌，加热回流反应，TLC跟踪反应，直到1-芘甲醛反应完为止，蒸发溶剂，获得粗品，再经纯化，即得目标产品。
较好地，按摩尔体积比计，1-芘甲醛∶肼基苯甲酸∶无水乙醇∶冰乙酸= 1mmoL∶1~1.5 mmoL∶30~45mL∶1~2mL。
所述芘-肼基苯甲酸作为三阶非线性光学材料的应用。
有益效果：
本发明所述芘-肼基苯甲酸合成条件温和，步骤简单，易于提纯，为设计合成其他具有三阶非线性的芘-肼基酸类化合物提供了参考。此外，本发明中的两个化合物通过飞秒激光Z扫描测试，结果表明化合物有很好的三阶非线性，在三阶非线性光学材料方面具有潜在的应用价值。
附图说明
图1：化合物1~2(1.0×10-5M)在DMF中的紫外可见吸收光谱，1-化合物1，2-化合物2。
图2：化合物1（1mg/ml）在515 nm波长飞秒激光下的开孔Z扫描曲线。
图3：化合物2（1mg/ml）在515 nm波长飞秒激光下的开孔Z扫描曲线。
图4：溶剂DMF的开孔Z扫描曲线。
具体实施方式
实施例1
化合物1的结构式为：
；
化合物1的合成路线如下：
；
化合物1的合成步骤：室温搅拌下，将1 mmol的1-芘甲醛溶于30 mL的乙醇中，再向其中加入1.5 mmol的3-肼基苯甲酸、2 mL 冰乙酸，加热回流反应，TLC跟踪反应，直到1-芘甲醛近乎反应完为止，蒸发溶剂，得棕色固体，用纯石油醚(PE)装硅胶柱，以石油醚(PE)和乙酸乙酯(EA)作为洗脱剂，收集V（PE）∶V（EA） =1∶1的洗脱剂，旋转蒸发溶剂，得化合物1。
化合物1的表征如下:1H NMR (400 MHz, DMSO-d 6, TMS): δH 7.47 – 7.31 (m,3H); 7.79 (s, 1H); 8.09 (t, 1H); 8.21 (d, 2H); 8.39 – 8.21 (m, 4H); 8.59 (d,1H); 8.76 (d, 1H); 8.95 (s, 1H); 10.86 (s, 1H)；13C NMR (400 MHz, DMSO-d6): δC 143, 136.81，131.78, 131.50, 131.27, 130.79, 128.73, 127.97, 126.97, 126.19,125.76, 124.83, 124.56,122.91, 115.2,114.4,110.2。
实施例2
化合物2的结构式为：
；
化合物2的合成路线如下：
；
化合物2的合成步骤：室温搅拌下，将1 mmol的1-芘甲醛溶于30 mL的乙醇中，再向其中加入1.5 mmol的4-肼基苯甲酸、2 mL 冰乙酸，加热回流反应，TLC跟踪反应，直到1-芘甲醛近乎反应完为止，蒸发溶剂，得棕色固体，用纯石油醚(PE)装硅胶柱，以石油醚(PE)和乙酸乙酯(EA)作为洗脱剂，收集V（PE）∶V（EA）=1∶1的洗脱剂，旋转蒸发溶剂，得化合物2。
化合物2的表征如下：1 H NMR (400 MHz, DMSO-d 6, TMS): δH 7.26 (d, 2H);7.91 (d, 2H); 8.10 (t, 1H); 8.23 – 8.15 (m, 2H); 8.33 (d, 4H); 8.62 (d, 1H);8.75 (d, 1H); 9.02 (s, 1H); 11.15 (s, 1H)；13C NMR (400 MHz, DMSO-d6): δC 149,137.88，131.78, 131.50, 131.27, 130.79, 128.73, 127.97, 126.97, 126.19,125.76, 124.83, 124.56, 122.91, 111.88。
将化合物1~2分别配成浓度为1.0×10-5 mol/L 的DMF溶液，测定其紫外吸收。化合物1~2在DMF中(1.0×10-5M)的紫外可见吸收光谱见图1。由图可知：从化合物1到化合物2，它们的吸收峰位置依次为412nm、417nm。
采用飞秒激光Z扫描方法对化合物1~2分别进行三阶非线性吸收特性研究：激光器输出的波长为515 nm，脉宽为260 fs，抽取1mL浓度为1×10-5 mol/L的化合物的DMF溶液，注入到厚度为2 mm的石英比色皿中，然后把比色皿放置到载物平移台上进行测量，凸透镜焦距为300 mm，焦点处的激光能量为40 nj，在上述条件下，对化合物的DMF溶液做开孔Z扫描研究，并对数据进行拟合。另外，以等量的DMF代替上述化合物的DMF溶液，对溶剂DMF做开孔Z扫描研究，并对数据进行拟合。
化合物1的开孔Z扫描曲线如图2所示。化合物1表现为反饱和吸收，透过率是0.9，三阶非线性吸收系数β=3.5×10-13 m/W。
化合物2的开孔Z扫描曲线如图3所示。化合物2表现为反饱和吸收，透过率是0.92，三阶非线性吸收系数β=7.2×10-13 m/W。
溶剂DMF的开孔Z扫描曲线如图4所示。DMF溶液的透过率是93%，β值为：0。
实验结果显示：
由于化合物 1~2在515 nm附近内无紫外吸收现象（见图1），由此确定515 nm激光波长下的产生三阶非线性吸收的原因不是由于紫外线性吸收所致，也不是溶剂DMF所致（见图4），而是化合物1~2本身所致。
比较本发明中的两个化合物，发现吸电子基的位置对三阶非线性吸收有影响，当羧基处于受体的对位时，有利于电子从给体向受体的传递，从而使非线性吸收系数有所增大。
上述实施例用来解释说明本专利，而不是对本专利进行限制，在本专利的精神和权利要求的保护范围内，对本专利作出的任何修改和改变，都落入本专利的保护范围。
Claims (4)
1.芘-肼基苯甲酸，其特征在于，所述芘-肼基苯甲酸为化合物1或化合物2，化合物1~2的结构式分别为：
、。
2.制备如权利要求1所述芘-肼基苯甲酸的方法，其特征在于：将1-芘甲醛溶解在无水乙醇中，再加入肼基苯甲酸和冰乙酸，搅拌，加热回流反应，TLC跟踪反应，直到1-芘甲醛反应完为止，蒸发溶剂，获得粗品，再经纯化，即得目标产品。
3.如权利要求2所述方法，其特征在于：按摩尔体积比计，1-芘甲醛∶肼基苯甲酸∶无水乙醇∶冰乙酸= 1mmoL∶1~1.5 mmoL∶30~45mL∶1~2mL。
4.如权利要求1所述芘-肼基苯甲酸作为三阶非线性光学材料的应用。
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| CN101852996A (zh) * | 2009-03-31 | 2010-10-06 | 京瓷美达株式会社 | 单层型电子照相感光体和图像形成装置 |
| WO2014148579A1 (ja) * | 2013-03-22 | 2014-09-25 | 三菱化学株式会社 | 電子写真感光体及び画像形成装置 |
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| CN101852996A (zh) * | 2009-03-31 | 2010-10-06 | 京瓷美达株式会社 | 单层型电子照相感光体和图像形成装置 |
| WO2014148579A1 (ja) * | 2013-03-22 | 2014-09-25 | 三菱化学株式会社 | 電子写真感光体及び画像形成装置 |
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| Study of Third-Order Optical Nonlinearities of Substituted Hydeazones in PMMA;S. Vijayakumar等;《Journal of Applied polymer Scienece》;20100727;第119卷;第596页图1 |
| 芘衍生物的三阶非线性光学性质研究;盛宁等;《济宁学院学报》;20130630;第34卷(第3期);第9页左栏倒数第2-7行 |
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