CN110437642A - 一种新型N-乙基Cy5菁染料及其合成方法与应用 - Google Patents
一种新型N-乙基Cy5菁染料及其合成方法与应用 Download PDFInfo
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- 239000000975 dye Substances 0.000 title claims abstract description 70
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title claims abstract description 66
- 238000010189 synthetic method Methods 0.000 title claims abstract description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 72
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N alpha-methyl acrolein Natural products CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims 1
- 150000002500 ions Chemical class 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 229910021645 metal ion Inorganic materials 0.000 description 19
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002189 fluorescence spectrum Methods 0.000 description 6
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 206010028980 Neoplasm Diseases 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
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Abstract
本发明涉及一种新型N‑乙基Cy5菁染料及其合成方法与应用,所述新型N‑乙基Cy5菁染料结构如下：其中可用于在乙腈溶液中检测Cu2+。
Description
技术领域
本发明属于菁染料领域，具体涉及一种新型N-乙基Cy5菁染料及其合成方法与应用。
背景技术
菁染料不是普通的织物染料，而是作为一种具有特殊功能的荧光染料，其摩尔消光系数较大，吸收波长在紫外可见光至近红外区间内，起初被作为一种卤化银凝胶的增感剂应用于感光材料领域中，现在被广泛应用于生物领域如蛋白检测、跟踪标记与显像成像中。随着生命科学研究的飞速发展，以荧光标识技术为核心的各项分析技术也逐渐增多，如生物分析、生物成像和疾病(特别是肿瘤)的机理分析和治疗等技术，对于上述分析技术中，荧光探针的设计与研究是至关重要的，而在荧光探针中扮演着重要角色的恰恰是荧光染料。因此，人们对于新型菁染料的研究越来越多。
发明内容
本发明提供一种新型N-乙基Cy5菁染料，其特征在于所述新型N-乙基Cy5菁染料结构如下：
本发明的另一实施方案提供上述新型N-乙基Cy5菁染料的合成方法，其特征在于包括如下步骤：
与(3-丙烯醛缩苯胺)在醋酸、醋酐作用下反应即得
该反应优选在100-110℃下反应4-6h。
与3-丙烯醛缩苯胺的摩尔比优选为1:0.5-0.6。醋酐与醋酸的体积比为1:1，每摩尔 使用醋酐6-7mL。
本发明的另一实施方案提供上述新型N-乙基Cy5菁染料(尤其是N-乙基Cy5菁染料)在检测Cu2+中的应用。
本发明的另一实施方案提供上述新型N-乙基Cy5菁染料(尤其是N-乙基Cy5菁染料)在乙腈溶液中检测Cu2+中的应用。
本发明的另一实施方案提供上述新型N-乙基Cy5菁染料(尤其是N-乙基Cy5菁染料)在制备Cu2+检测试纸中的应用。
附图说明
图1是5-磺酸基N-乙基Cy5菁染料1H NMR谱图。
图2是N-乙基Cy5菁染料1H NMR谱图。
图3是5-磺酸基N-乙基Cy5菁染料在7种溶剂中的紫外-可见光谱谱图。
图4是N-乙基Cy5菁染料在9种溶剂中的紫外-可见光谱谱图。
图5是5-磺酸基N-乙基Cy5菁染料在乙腈溶剂中加入金属离子的紫外可见和荧光光谱谱图。
图6是5-磺酸基N-乙基Cy5菁染料在乙醇溶剂中加入金属离子的紫外可见和荧光光谱谱图。
图7是N-乙基Cy5菁染料在乙腈溶剂中加入金属离子的紫外可见和荧光光谱谱图。
图8是N-乙基Cy5菁染料在丙酮溶剂中加入金属离子的紫外可见和荧光光谱谱图。
图9是N-乙基Cy5基菁染料乙腈溶液滴加金属离子显色图。
图10是Cu2+离子滴定N-乙基Cy5基菁染料的紫外可见光谱谱图。
图11是N-乙基Cy5菁染料Cu2+离子检测试纸图。
具体实施方式
为了便于对本发明的进一步理解，下面提供的实施例对其做了更详细的说明。但是这些实施例仅供更好的理解发明而并非用来限定本发明的范围或实施原则，本发明的实施方式不限于以下内容。
实施例1
取(CAS登记号474972-44-6，2mmol)、3-丙烯醛缩苯胺(CAS登记号：4485-89-6，1.0mmol)，加入醋酸(12mL)、醋酐(12mL)，搅拌下加热至110℃，反应4h后，减压浓缩，经硅胶柱层析，得5-磺酸基N-乙基Cy5菁染料(1.47g，收率约为94.9％)，1H NMR(400MHz，DMSO-d6)，δ:8.29(t，1H，J＝11.0Hz，CH＝CH),7.76(s，2H，Ar-H)，7.65(d，2H，J＝8.0Hz，Ar-H)，7.35(d，2H，J＝4.4Hz，Ar-H)，6.64(d，4H，J＝12.0Hz，CH＝CH)，4.25-4.35(m，4H，N-CH2)，1.67(s，12H,C(CH3)2).详见图1。
实施例2
取(CAS登记号14134-81-7,2mmol)、3-丙烯醛缩苯胺(1.2mmol)，加入醋酸(14mL)、醋酐(14mL)，搅拌下加热至100℃，反应6h后，减压浓缩，经硅胶柱层析得N-乙基Cy5菁染料(5.15g，收率约为96.3％)。1H NMR(400MHz，DMSO-d6)，δ:8.28(t，1H，J＝11.0Hz，CH＝CH),7.76(s,2H，Ar-H)，7.64(d，2H，J＝8.0Hz，Ar-H)，7.36(d，2H，J＝4.4Hz，Ar-H)，6.65-6.62(d，4H，J＝12.0Hz，CH＝CH)，4.20-4.35(m，4H，N-CH2)，1.67(s，12H,C(CH3)2).详见图2。
实施例3两种菁染料光谱研究
5-磺酸基N-乙基Cy5菁染料在乙腈、乙醇、水、甲醇、DMSO、DMF和丙酮七种溶剂中溶解性较好。，紫外-可见光谱谱图如图3。
N-乙基Cy5菁染料在乙酸乙酯、四氢呋喃、乙腈、乙醇、氯仿、甲醇、DMSO、DMF和丙酮九种有机溶剂中溶解性较好，紫外-可见光谱谱如图4。
(1)5-磺酸基N-乙基Cy5菁染料乙腈中离子检测
5-磺酸基N-乙基Cy5菁染料在乙腈溶剂中加入金属离子的紫外可见和荧光光谱谱图(见图5)，由图5可知，5-磺酸基N-乙基Cy5菁染料在乙腈溶液中，由多个金属离子发生了荧光淬灭，同时紫外可见吸收谱图中由一个峰变成了两个峰。这是因为在乙腈溶液中，菁染料一般为单聚体的形式存在，当加入金属离子后，单聚体变成了二聚体甚至是多聚体，从而导致谱图的变化及菁染料乙腈溶液的颜色变化。但是加入金属离子后菁染料本身没有发生变化，只是物质聚集状态发生了变化，并且有多个金属离子使它发生了变化，所以无法说明磺酸基菁染料对哪个金属离子有识别能力。
(2)5-磺酸基N-乙基Cy5菁染料乙醇中离子检测
5-磺酸基N-乙基Cy5菁染料在乙醇溶剂中加入金属离子的紫外可见和荧光光谱谱图(见图6)，由图6可知，5-磺酸基N-乙基Cy5菁染料在乙醇溶液中加入金属离子后，其谱图没有发生任何变化，说明在乙醇溶剂中，5-磺酸基N-乙基Cy5菁染料对以上二十余种金属离子都没有识别和检测能力。
(3)N-乙基Cy5菁染料乙腈中离子检测
N-乙基Cy5菁染料在乙腈溶剂中加入金属离子的紫外可见和荧光光谱谱图(见图7)，由图7可知，N-乙基Cy5菁染料在乙腈溶液中，只有加入Cu2+离子后其光谱发生了变化，而加入其他金属离子并未对菁染料有影响。经观察，在N-乙基Cy5菁染料乙腈溶液内滴加Cu2+离子后颜色褪去接近无色透明，由此可以证明，N-乙基Cy5菁染料在乙腈溶液中对Cu2+离子有着特殊的识别能力。
(4)N-乙基Cy5菁染料丙酮中离子检测
N-乙基Cy5菁染料在丙酮溶剂中加入金属离子的紫外可见和荧光光谱谱图(见图8)，由图8可知，N-乙基Cy5菁染料在丙酮溶液中，只有加入Cu2+离子后其光谱发生变化，其他金属离子没有发生变化。但是，经观察，在N-乙基Cy5菁染料丙酮溶液内滴加Cu2+离子后其颜色变化并不明显，增大Cu2+离子的浓度也没有明显变化。由此得出，虽然加入Cu2+离子后对其谱图有着一定的影响，但是肉眼观察并没有特别明显的变化，故说明N-乙基Cy5菁染料在丙酮溶液中对Cu2+离子的识别能力并没有那么强，无法胜任对Cu2+离子进行识别检测的工作。
由以上实验可知，只有N-乙基Cy5菁染料在乙腈溶液中对Cu2+离子有着特殊的识别能力，可用于检测Cu2+离子(见图9)。
实施例4滴定实验
由实施例3可知在N-乙基Cy5菁染料乙腈溶液中滴加Cu2+离子后颜色褪去至无色，滴定实验就是确定具体多少浓度的Cu2+离子即可使N-乙基Cy5菁染料乙腈溶液褪色。滴定结果如图10。
当Cu2+离子浓度不断增大时，紫外波峰不断降低，其紫外吸收波长也不断减小，这是因为滴加Cu2+离子之后，Cu2+离子对N-乙基Cy5菁染料本身发生了反应，不仅使紫外可见吸收波长发生变化，同时也使溶液颜色褪色至无色。通过浓度梯度滴加Cu2+离子直至新生成的波峰不再发生变化，记录Cu2+离子的浓度为1×10-2mol/L，即在1×10-5mol/L的N-乙基Cy5菁染料乙腈溶液中，1×10-2mol/L浓度的Cu2+离子可使溶液颜色褪至无色。
实施例5检测试纸的制作
①配置浸泡液，取一试管，配置1×10-5mol/L的N-乙基Cy5菁染料乙醇溶液，使菁染料在乙醇中完全溶解并且配置好的溶液颜色够深，以在光下目测不可透光为最好。
②裁剪试纸，取一块滤纸，用剪刀裁剪成数条1cm×5cm规格的纸条，使纸条可以完全浸泡在染料溶液内。静置一段时间，使染料充分浸染到试纸上。
③取出试纸，晾干并选取颜色分布均匀的纸条，将其裁剪成规格为1cm×1cm的纸片，取一块够大且表面干净平整的玻璃板，在玻璃板下放一块大小相近的白纸，将裁减好的纸片均匀放在玻璃板上，分别滴加一定量的金属离子溶液，溶液要求完全浸湿纸片即可。等被金属离子溶液浸湿的纸片晾干后，滴加乙腈，使乙腈将纸片完全浸湿。静置晾干观察是否有颜色变化(见图11)。
Claims (7)
1.一种新型N-乙基Cy5菁染料，其特征在于所述新型N-乙基Cy5菁染料结构如下：
2.权利要求1所述的新型N-乙基Cy5菁染料的合成方法，其特征在于包括如下步骤：
与(3-丙烯醛缩苯胺)在醋酸、醋酐作用下反应即得
3.权利要求2所述的合成方法，其特征在于该反应优选在100-110℃下反应4-6h。
4.权利要求2-3任一项所述的合成方法，其特征在于
与3-丙烯醛缩苯胺的摩尔比优选为1:0.5-0.6。醋酐与醋酸的体积比为1:1，每摩尔使用醋酐6-7mL。
5.权利要求1所述的新型N-乙基Cy5菁染料(尤其是N-乙基Cy5菁染料)在检测Cu2+中的应用。
6.权利要求1所述的新型N-乙基Cy5菁染料(尤其是N-乙基Cy5菁染料)在乙腈溶液中检测Cu2+中的应用。
7.权利要求1所述的新型N-乙基Cy5菁染料(尤其是N-乙基Cy5菁染料)在制备Cu2+检测试纸中的应用。
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