CN104610310B - 一种具有荧光性能的苯并咪唑衍生物-镉(ii)配合物及其合成方法 - Google Patents
一种具有荧光性能的苯并咪唑衍生物-镉(ii)配合物及其合成方法 Download PDFInfo
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Abstract
本发明公开了一种具有荧光性能的苯并咪唑衍生物‑镉(II)配合物及其合成方法,本发明所述的具有荧光性能的柔性苯并咪唑衍生物配合物的结构为:本发明所采用的技术方案为以稀盐酸作溶剂合成的一种苯并咪唑衍生物作为第一配体,以H2O–甲醇–DMF(N,N‑二甲基甲酰胺)为溶剂,通过溶剂热法合成镉金属配合物。本发明在低温下即可合成配体,且此配体有较强的配位能力、灵活多变的配位模式,具有荧光性能的{[Cd(immb)I2]·DMF}n配合物结构独特,合成技术简单、安全,产物纯度高,且测量方法准确新颖。
Description
技术领域
本发明属于配位化学领域,具体涉及到一种苯并咪唑类配合物;同时涉及到一种苯并咪唑类配合物的合成方法。
背景技术
配位化学是研究金属原子或离子与无机、有机离子或分子相互反应形成配位化合物的特点以及它们的成键、结构、反应、分类和制备的一门学科。
苯并咪唑及其衍生物是一类优良的有机桥联配体,通过与金属离子进行自组装得到具有新颖结构的配合物。苯并咪唑衍生物因其具有较强的配位能力、灵活多变的配位模式以及在光电、催化、磁性、抗癌、抗菌、消炎等领域的广泛用途而成为一类优良的有机配体,因此设计、合成具有新奇结构和特殊性能的苯并咪唑及其衍生物类配合物有着重要的科学意义和实用价值。
发明内容
本发明的目的在于提供一种具有荧光性能的柔性苯并咪唑衍生物配合物,并提供其制备方法。
本发明所采用的技术方案为以稀盐酸作溶剂合成的一种苯并咪唑衍生物作为配体,以H2O–DMF(N,N-二甲基甲酰胺)为溶剂,通过溶剂热法合成镉金属配合物。
本发明所述的具有荧光性能的柔性苯并咪唑衍生物配合物的结构见图1所示。
本发明用于制备所述配合物的合成方法包括以下步骤:
a、配体2-(1H-咪唑-1-甲基)-6-甲基-1H-苯并咪唑(immb)的合成:
分别称取3,4-二氨基甲苯(0.1-0.5 mol),1-咪唑-1-乙酸 (0.12-0.60 mol)加入到250-1000 mL的三口烧瓶中,再加入75-375 mL 4 mol/L的盐酸作溶剂,在室温下搅拌10-20 h,溶液呈红褐色,然后在100 ℃下回流10-15 h,溶液逐渐加深,最后为深褐色。冷却后,将反应液倾入200-1000 mL的蒸馏水中,用氨水调节pH = 7~8有大量沉淀析出,抽滤,然后用热水重结晶,得到黄色晶体;
b、配合物{[Cd(immb)I2]·DMF}n的合成:
将1-4mL immb配体(0.05-0.2mmol)的DMF (N,N-二甲基甲酰胺)溶液逐滴滴加到2-8 mL CdI2(0.05-0.2mmol)的水溶液中,再将该混合溶液放入反应釜中,置于烘箱内,恒温80℃反应72-80 h,以5-10℃/h的速度降至室温,有浅黄色块状晶体析出,得到配合物{[Cd(immb)I2]·DMF}n ,产率:41%。
本发明的有益效果如下:低温下即可合成配体,且此配体有较强的配位能力、灵活多变的配位模式,具有荧光性能的{[Cd(immb)I2]·DMF}n配合物结构独特,合成技术简单、安全,产物纯度高,且测量方法准确新颖。
附图说明
图1是配合物{[Cd(immb)I2]·DMF}n的一维结构图。
图2是immb配体的Mulliken电荷分布及潜在配位模式。
图3是配合物{[Cd(immb)I2]·DMF}n的配位环境图。
图4是配合物{[Cd(immb)I2]·DMF}n中π-π堆积作用。
图5是配合物{[Cd(immb)I2]·DMF}n的三维结构。
图6是配合物{[Cd(immb)I2]·DMF}n的XRD图谱。
图7是配合物{[Cd(immb)I2]·DMF}n及相应配体(immb)的固态荧光。
具体实施方式
本发明以下将结合实施例作进一步描述:
本发明所述的具有荧光性能的柔性苯并咪唑衍生物配合物的结构见图1所示。
实施例1
a、配体2-(1H-咪唑-1-甲基)-6-甲基-1H-苯并咪唑(immb)的合成
分别称取3,4-二氨基甲苯13.44 g (0.11 mol),1-咪唑-1-乙酸16.39 g (0.13 mol)加入到250mL的三口烧瓶中,再加入75mL 4 mol/L的盐酸作溶剂,在室温下搅拌10 h,溶液呈红褐色,然后在100℃下回流10 h,溶液逐渐加深,最后为深褐色。冷却后,将反应液倾入200mL的蒸馏水中,用氨水调节pH = 7~8有大量沉淀析出,抽滤,然后用热水重结晶,得到黄色晶体9.07 g (产率:38.87%)
b、配合物{[Cd(immb)I2]·DMF}n的合成
将1mL immb配体(0.05mmol)的DMF (N,N-二甲基甲酰胺)溶液逐滴滴加到2mL CdI2(0.05mmol)的水溶液中,再将该混合溶液放入反应釜中,置于烘箱内,恒温80℃反应72 h,以10℃/h的速度降至室温,有浅黄色块状晶体析出,得到配合物{[Cd(immb)I2]·DMF}n (产率:41%)。
实施例2
a、配体2-(1H-咪唑-1-甲基)-6-甲基-1H-苯并咪唑(immb)的合成:
分别称取3,4-二氨基甲苯25.66 g (0.21 mol),1-咪唑-1-乙酸31.53 g (0.25mol)加入到500 mL的三口烧瓶中,再加入150 mL 4 mol/L的盐酸作溶剂,在室温下搅拌15 h,溶液呈红褐色,然后在100 ℃下回流12 h,溶液逐渐加深,最后为深褐色。冷却后,将反应液倾入500 mL的蒸馏水中,用氨水调节pH = 7~8有大量沉淀析出,抽滤,然后用热水重结晶,得到黄色晶体17.32 g (产率:38.86%)。
b、配合物{[Cd(immb)I2]·DMF}n的合成
将2mL immb配体(0.1mmol)的DMF (N,N-二甲基甲酰胺)溶液逐滴滴加到4mL CdI2(0.1mmol)的水溶液中,再将该混合溶液放入反应釜中,置于烘箱内,恒温80℃反应75 h,以5℃/h的速度降至室温,有浅黄色块状晶体析出,得到配合物{[Cd(immb)I2]·DMF}n (产率:40%)。
实施例3
a、配体2-(1H-咪唑-1-甲基)-6-甲基-1H-苯并咪唑(immb)的合成:
分别称取3,4-二氨基甲苯48.87 g (0.4 mol),1-咪唑-1-乙酸63.05 g (0.5 mol)加入到1000 mL的三口烧瓶中,再加入375 mL 4 mol/L的盐酸作溶剂,在室温下搅拌20 h,溶液呈红褐色,然后在100 ℃下回流15 h,溶液逐渐加深,最后为深褐色。冷却后,将反应液倾入1000 mL的蒸馏水中,用氨水调节pH = 7~8有大量沉淀析出,抽滤,然后用热水重结晶,得到黄色晶体33.02g (产率:38.89%)。
b、配合物{[Cd(immb)I2]·DMF}n的合成
将4mL immb配体(0.2mmol)的DMF (N,N-二甲基甲酰胺)溶液逐滴滴加到8mL CdI2(0.2mmol)的水溶液中,再将该混合溶液放入反应釜中,置于烘箱内,恒温80℃反应80 h,以5℃/h的速度降至室温,有浅黄色块状晶体析出,得到配合物{[Cd(immb)I2]·DMF}n (产率:41%)。
本发明配体immb的量化计算结果表明,存在三个潜在的氮原子配位点,N4,N1及N2的Mulliken电荷分布分别为-0.451,-0.543和-0.644。配体immb中的N2上有质子存在。因此在适合的反应条件下,配体immb具有较强的配位能力及灵活多变的配位模式(图2)。
X-射线单晶衍射结果分析表明,配合物属于单斜晶系,P21/c空间群,为一维结构,结构中所有的Cd(II)都是等价的。Cd(II)离子周围的配位环境如图3所示,一个不对称单元中包含一个四配位的Cd(II)离子、两个配位的碘离子、一个immb配体(immb配体上的甲基无序)和一个游离的DMF分子。中心金属Cd(II)处于一个扭曲的四面体配位环境中,四个顶点分别被两个碘离子和两个来自于两个immb的N原子所占据(Cd(1)-N(4)#1: 2.240(8) Å,
Cd(1)-N(1): 2.255(7) Å, Cd(1)-I(1): 2.7019(12) Å, Cd(1)-I(2): 2.7447(12) Å),该键长均属于正常的配位键。
在配合物中,配体immb以二齿桥联模式与Cd(II)配位,如图(1)所示,配体immb以二齿桥联模式沿c方向连接Cd(II)离子形成一维链状结构,Cd···Cd之间的距离为8.2523(18) Å。如图(4)所示,相邻链间的苯环质心之间的距离为3.75 Å,说明它们之间存在弱的π-π堆积作用。另外,immb配体上NH基团与游离的DMF分子之间可以形成N-H···O氢键(N(2)-H(2B)···O(1): 1.89 Å) (图5)。一维链结构正是通过N-H···O氢键和π-π堆积作用进一步形成了稳定的三维超分子结构。
对所合成的配合物进行粉末X-射线衍射(XRD)图谱分析来表征配合物的纯度。结果显示实验得到的配合物的XRD图谱与模拟的图谱基本吻合(图6),这说明配合物的纯度较高。
图7所示是配合物及相应配体的固态荧光,配体immb的荧光发射峰位于310 nm (λex = 268 nm),它的荧光来自π*→π的电荷跃迁。配合物{[Cd(immb)I2]·DMF}n的荧光发射峰为316 nm (λex = 273 nm),与配体immb的峰位置相近,该荧光峰来自于配体内的π*→π的电荷跃迁。另外,由于碘离子I-对荧光有淬灭作用,配合物的荧光强度低于配体immb。
Claims (2)
1.一种具有荧光性能的苯并咪唑衍生物-镉(II)配合物,其特征在于:所述配合物的结构为{[Cd(immb)I2]·DMF}n,配合物属于单斜晶系,P21/c空间群,为一维结构,结构中所有的Cd(II)都是等价的;一个不对称单元中包含一个四配位的Cd(II)离子、两个配位的碘离子、一个immb配体和一个游离的DMF分子,immb为2-(1H-咪唑-1-甲基)-6-甲基-1H-苯并咪唑,配体上的甲基无序;中心金属Cd(II)处于一个扭曲的四面体配位环境中,四个顶点分别被两个碘离子和两个来自于两个immb的N原子所占据;配体immb以二齿桥联模式沿c方向连接Cd(II)离子形成一维链状结构,Cd···Cd之间的距离为8.2523(18) Å;一维链结构通过N-H···O氢键和相邻苯环间π-π堆积作用进一步形成稳定的三维超分子结构。
2.一种制备权利要求1所述配合物的方法,其特征在于:所述方法包括以下步骤:
a、配体2-(1H-咪唑-1-甲基)-6-甲基-1H-苯并咪唑(immb)的合成:
分别称取3,4-二氨基甲苯0.1-0.5 mol,1-咪唑-1-乙酸0.12-0.60 mol加入到250-1000 mL的三口烧瓶中,再加入75-375 mL 4 mol/L的盐酸作溶剂,在室温下搅拌10-20 h,溶液呈红褐色,然后在100 ℃下回流10-15 h,溶液颜色逐渐加深,最后为深褐色;冷却后,将反应液倾入200-1000 mL的蒸馏水中,用氨水调节pH=7~8,有大量沉淀析出,抽滤,然后用热水重结晶,得到黄色晶体;
b、配合物{[Cd(immb)I2]·DMF}n的合成:
将1-4 mL含有0.05-0.2 mmol配体immb的DMF溶液逐滴滴加到2-8 mL CdI2的水溶液中,再将该混合溶液放入反应釜中,置于烘箱内,恒温80℃反应72-80h,以5-10℃/h的速度降至室温,有浅黄色块状晶体析出,得到配合物{[Cd(immb)I2]·DMF}n。
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