CN103555319A - 含氟环丙喹啉希夫碱蓝色发光材料及其制备方法 - Google Patents
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Abstract
本发明公开了一种式I所示的含氟环丙喹啉希夫碱蓝色发光材料及其制备方法。本发明所述的发光材料可由2-环丙基-4-氟苯基喹啉-3-甲醛和三氨乙基胺反应得到。本发明发的制备方法简单，原料易得，所制备的含氟环丙喹啉希夫碱在紫外光激发下呈现良好的蓝色发光特性，特别是在固态时具有更高的荧光发射强度。可用于研制荧光探针、荧光防伪材料，也可作为刺激响应功能材料应用于化学/生物传感器。
Description
技术领域：
本发明属于有机发光材料技术领域，具体涉及含氟环丙喹啉希夫碱蓝色发光材料及其制备方法。
背景技术：
有机发光材料广泛应用于有机电致发光器件、有机固体激光器、有机光伏电池以及有机荧光传感器等领域。设计开发具有高荧光效率、不同发射波长、强的固态荧光发射的有机发光材料，是当前光子学材料与技术领域研究的一个热点。
喹啉类化合物是重要的荧光化合物，这类化合物具有优异的光物理特性和较高的荧光量子产率，已被应用于发光器件、光伏电池、荧光探针等领域之中。孙一峰等最近在专利（CN 103265531 A）中公开了一种氟代苯基喹啉咪唑化合物，该化合物具有蓝色发光特性，对氟离子和碱具有敏感特性，可用于发光器件和荧光敏感领域。
三（2-氨乙基）胺及其衍生物常用作有机配体、有机合成中间体、螯合剂、缓蚀剂等，其最为突出的结构特点就是分子中含有多个强配位氮原子，能够形成多种立体配位结构，从而影响配合物的性能。这类基于三（2-氨乙基）胺的配合物的合成、光电特性及应用研究引起了人们的关注，并开展了广泛的研究。最近，Yang 等（Tian-Lin Yang, Wen-Wu Qin，Synthesis and novel fluorescence phenomenon of terbium complex with a new Schiff base ligand derived from condensation of triaminotriethylamine and 3-indolemethanal，Spectrochimica Acta Part A, 2007, 67 568–571）研究了吲哚缩三氨乙基胺希夫碱铽配合物的荧光特性；Zhou 等（Ying Zhou, Ji Young Jung, Hye Ryeong Jeon, Youngmee Kim, Sung-Jin Kim, Juyoung Yoon，A novel supermolecular tetrameric vanadate-selective colorimetric and “Off-On” sensor with pyrene Ligand，Organic Letters，2011,13,2742-2745）合成了新的三氨乙基胺希夫碱，并成功用作四聚钒酸盐的荧光敏感器；McDaniel 等（Ashley M. McDaniel, Huan-Wei Tseng, Ethan A. Hill, Niels H. Damrauer, Anthony K. Rappe?, Matthew P. Shores, Syntheses and photophysical investigations of Cr(III) hexadentate iminopyridine complexes and their tris(bidentate) analogues，Inorg. Chem. 2013, 52, 1368?1378）研究了三氨乙基胺希夫碱铬配合物的光物理特性。
然而，这些研究更多关注三氨乙基胺希夫碱配合物的光物理性能，而对三氨乙基胺希夫碱本身的性能，尤其是固态荧光特性的关注较少，这可能是由于多数三氨乙基胺希夫碱的固态荧光较弱或没有荧光。
再者，通过2-环丙基-4-氟苯基喹啉-3-甲醛与三（2-氨乙基）胺反应，形成含氟环丙喹啉希夫碱，并考察其发光特性，在现有的技术中尚未见报道。
发明内容：
本发明的目的之一在于提供一种含氟环丙喹啉希夫碱蓝色发光材料。
本发明是通过以下技术方案实现的：
含氟环丙喹啉希夫碱蓝色发光材料的结构如式I所示： 
。
本发明的另一目的是提供上述蓝色发光材料的制备方法。
本发明所述的有机发光材料的合成路线如下：
将摩尔比为1:3～3.3的三氨乙基胺（化合物Ⅲ）和2-环丙基-4-氟苯基喹啉-3-甲醛（化合物Ⅱ）溶于有机溶剂中，在氮气保护下，搅拌回流反应4~7小时，得到目标产物。
所述有机溶剂为甲醇或乙醇或氯仿或二氯甲烷或甲苯。
本发明在分子中引入了环丙基，一方面加强了化合物共轭体系中的推电子作用；另一方面环丙基的引入能够有效增加分子的空间位阻，减少高浓度时分子间相互作用，防止浓度猝灭；同时，环丙基的引入还可以增加三取代咪唑化合物的溶解度。
本发明的含氟环丙喹啉希夫碱化合物的氯仿溶液以及其固态粉末，在紫外光激发下，均发射出476 nm的蓝色荧光，特别是在固体状态时具有更高的荧光发射强度。
本发明的化合物具有溶致荧光变色作用，随着溶剂极性增大，其荧光发射峰依次红移，荧光发射颜色由蓝色逐渐变为绿色，其发光颜色可以通过选择不同的溶剂进行调节。
本发明的化合物固体粉末对酸性物质也具有响应作用，通过酸碱调节，能够实现荧光开关转变。
本发明的发光材料在荧光探针、荧光防伪材料，以及荧光化学/生物传感等领域具有潜在应用价值。
附图说明：
图1是实施例1得到的化合物在氯仿溶液中的紫外吸收和荧光光谱图；
图2是实施例1得到的化合物的固态荧光光谱图。
具体实施方式：
以下是对本发明的进一步说明，而不是对本发明的限制。
实施例1：含氟环丙喹啉希夫碱（化合物I）的制备
将三氨乙基胺（化合物Ⅲ）（0.01 mol）和2-环丙基4-氟苯基喹啉-3-甲醛（化合物Ⅱ）（0.03 mol）溶于35毫升甲醇中，在氮气保护下，搅拌回流反应5小时，减压蒸去甲醇，析出白色固体，粗产品用甲醇重结晶，得到目标产物，产率为71 %。熔点 86-88 ℃。
1H NMR (300 MHz, CDCl3/TMS) δ: 0.94-1.00(m, 6H), 1.30-1.36(m, 6H), 2.71(t, J = 6.9 Hz, 6H), 2.94-3.00(m, 3H), 3.52(t, J = 6.9 Hz, 6H), 7.11-7.25 (m, 12H), 7.29-7.39 (m, 6H), 7.61-7.67(m, 3H), 7.95(d, J = 8.4 Hz, 3H), 8.22 (s, 3H); 13C NMR (75 MHz, CDCl3/TMS) δ: 11.16, 14.79, 54.92, 60.50, 115.26, 115.54, 125.36, 125.64, 125.90, 127.33, 129.00, 129.84, 131.81, 131.85, 131.90, 132.01, 146.72, 147.59, 160.82, 160.90, 161.21, 164.18; 19F NMR (470 MHz, DMSO-d6) δ: -113.69。 IR (KBr) ν: 3064, 3003, 2838, 1645, 1605, 1557, 1513, 1489, 1415, 1223, 1159, 1067, 1022, 929, 842, 762, 627。ESI-MS m/z: 966.1 M-.
实施例2：磷杂菲基苯并噁唑化合物（化合物I）的制备
按实施例1的方法得到，不同的是，三氨乙基胺（化合物Ⅲ）和2-环丙基4-氟苯基喹啉-3-甲醛（化合物Ⅱ）的摩尔比为1 : 3.3，产率为67%。
实施例3：磷杂菲基苯并噁唑化合物（化合物I）的荧光性能测试
将实施例1得到的化合物I配制成浓度为1.28 × 10-4 M氯仿溶液，用1 厘米样品池在HORIBA Jobin Yvon Aqualog吸收和三维荧光扫描光谱仪上测定紫外吸收和荧光性能，结果如图1所示。同时测定固态发光光谱，激发波长为380 nm，结果见图2。
由图1可知，实施例1得到的化合物I分子在240 nm ~ 375 nm波段有三个吸收峰，其最大吸收峰位于249 nm，另两个较弱的吸收分别位于295nm及330 nm左右，而在大于375 nm以上波段无明显吸收。同时，实施例1得到的化合物I分子在氯仿溶液中，用360 nm光激发，其荧光发射峰位于476 nm，为蓝色发光。由图2可知，实施例1得到的化合物I的固体粉末，在波长为380 nm的光激发下，发出强的蓝色荧光，其发射峰为476 nm。其结果说明，该化合物在溶液中和固态时均具有蓝色发光特性。
进一步的研究发现，相同浓度的化合物I分子在正己烷、丙酮、四氢呋喃、乙醇及乙腈溶液中呈现蓝到绿色荧光，其荧光发射峰分别位于459、489、496、499、503 nm，说明该分子具有溶致变色效应。随着溶剂极性增大，其荧光发射峰依次红移，荧光发射颜色由蓝色逐渐变为绿色。结果说明，其发光颜色可以通过选择不同的溶剂进行调节，也可以利用化合物的这种溶致荧光变色行为,来探测分子环境极性的大小，因而可以用作荧光分子探针。
此外，该化合物的乙醇溶液对Ag+、Cu2+、Ce3+ 及乙酸具有识别作用，伴随着Ag+ 的添加，荧光发射峰发生明显蓝移，而Cu2+、Ce3+ 及乙酸的加入则会引起分子荧光的明显猝灭。
化合物固体粉末对酸性物质也具有识别作用，当固体粉末暴露于盐酸或乙酸气氛中数分钟之后，其蓝色荧光猝灭，而当再次置于氨水气氛中数分钟之后，其蓝色荧光恢复。化合物固体粉末与樟脑酸粉末混合研磨之后，其蓝色荧光也发生猝灭，而将此混合物暴露于氨水气氛中数分钟之后，其蓝色荧光恢复。因而可用于气敏和荧光传感领域。
Claims (4)
1.一种式Ⅰ所示的含氟环丙喹啉希夫碱蓝色发光材料：
。
2.一种权利要求1所述的含氟环丙喹啉希夫碱蓝色发光材料的制备方法，其特征在于将摩尔比为1:3～3.3的三氨乙基胺和2-环丙基-4-氟苯基喹啉-3-甲醛溶于有机溶剂中，在氮气保护下，搅拌回流反应4~7小时，得到目标产物。
3.根据权利要求2所述的含氟环丙喹啉希夫碱蓝色发光材料的制备方法，其特征在于，所述有机溶剂为甲醇或乙醇或氯仿或二氯甲烷或甲苯。
4.权利要求1所述的蓝色发光材料，应用于荧光探针、荧光防伪材料或化学/生物传感器。
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749403A (zh) * | 2016-12-08 | 2017-05-31 | 广东省测试分析研究所（中国广州分析测试中心） | 一种氟代苯基喹啉氧化膦阻燃发光双功能材料及其制备方法 |
| CN114835909A (zh) * | 2022-03-16 | 2022-08-02 | 桂林理工大学 | 一种兼具高稳定性与光刺激响应性的镝基单离子磁体超分子框架及其合成方法 |
| CN118598811A (zh) * | 2024-05-24 | 2024-09-06 | 东南大学 | 基于全可见光调控的水杨醛希夫碱固态双模光开关的制备和应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012002741A2 (en) * | 2010-07-01 | 2012-01-05 | Yuhan Corporation | Process for the preparation of hmg-coa reductase inhibitors and intermediates thereof |
| CN102875464A (zh) * | 2012-10-23 | 2013-01-16 | 桂林师范高等专科学校 | 3-希夫碱-2(1h)-喹啉酮衍生物及其制备方法和应用 |
| CN103265531A (zh) * | 2013-06-05 | 2013-08-28 | 中国广州分析测试中心 | 一种氟代苯基喹啉咪唑蓝色有机发光材料及其制备方法 |
-
2013
- 2013-10-25 CN CN201310508214.5A patent/CN103555319A/zh active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012002741A2 (en) * | 2010-07-01 | 2012-01-05 | Yuhan Corporation | Process for the preparation of hmg-coa reductase inhibitors and intermediates thereof |
| CN102875464A (zh) * | 2012-10-23 | 2013-01-16 | 桂林师范高等专科学校 | 3-希夫碱-2(1h)-喹啉酮衍生物及其制备方法和应用 |
| CN103265531A (zh) * | 2013-06-05 | 2013-08-28 | 中国广州分析测试中心 | 一种氟代苯基喹啉咪唑蓝色有机发光材料及其制备方法 |
Non-Patent Citations (3)
| Title |
|---|
| B. NISAR AHAMED: "A chelation enhanced selective fluorescence sensing of Hg2+ by a simple quinoline substituted tripodal amide receptor", 《DALTON TRANSACTIONS》 * |
| TIAN-LIN YANG等: "Synthesis and novel fluorescence phenomenon of terbium complex with a new Schiff base ligand derived from condensation of triaminotriethylamine and 3-indolemethanal", 《SPECTROCHIMICA ACTA PART A》 * |
| 费学宁: "《靶向生物荧光探针制备技术》", 30 March 2013, 科学出版社 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749403A (zh) * | 2016-12-08 | 2017-05-31 | 广东省测试分析研究所（中国广州分析测试中心） | 一种氟代苯基喹啉氧化膦阻燃发光双功能材料及其制备方法 |
| CN114835909A (zh) * | 2022-03-16 | 2022-08-02 | 桂林理工大学 | 一种兼具高稳定性与光刺激响应性的镝基单离子磁体超分子框架及其合成方法 |
| CN118598811A (zh) * | 2024-05-24 | 2024-09-06 | 东南大学 | 基于全可见光调控的水杨醛希夫碱固态双模光开关的制备和应用 |
| CN118598811B (zh) * | 2024-05-24 | 2025-05-06 | 东南大学 | 基于全可见光调控的水杨醛希夫碱固态双模光开关的制备和应用 |
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