CN106497544B - 一种基于二芳基乙烯的有机光致变色材料及其制备方法和应用 - Google Patents
一种基于二芳基乙烯的有机光致变色材料及其制备方法和应用 Download PDFInfo
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Abstract
本发明一种基于二芳基乙烯的有机光致变色材料,其结构式如通式I所示,通式I,其中,X为Cl、Br、I。本发明还提供了上述光致变色材料的制备方法,将具有光致变色性能的基于二芳基乙烯的单醛类化合物与氯化三氨基胍盐反应,待反应停止后过滤,洗涤,纯化得到基于二芳基乙烯的希夫碱的新型光开关分子化合物。本发明在离子作用下可以专一性地阻碍材料在光照环境中产生颜色和/或荧光的变化,可用于制备多寻址光电分子开关、分子导线元件和光致变色发光器件等。
Description
技术领域
本发明属于材料学领域,涉及一种有机光致变色材料,具体来说是一种基于二芳基乙烯的有机光致变色材料。
背景技术
随着科学技术的不断发展,发展海量信息存储材料与高速信息传输材料已成为现代信息技术发展的主要目标;在时间尺度上实现分子水平乃至原子水平上的信息存储也是现代信息技术的研究方向。对于有机光致变色材料而言,信息的读写均采用全光子模式,所以,设计制备高性能的有机光致变色材料一直是研究者追求的目标。光致变色现象是指一个化合物在受到一定波长的光照射时,可发生特定的化学反应,获得产物,在另一波长的光照射或者热的作用下,又恢复至原来的分子结构,具有这种性质的材料就称为光致变色材料。有机光致变色材料的种类繁多,其中,二芳基乙烯衍生物分子内的1,3,5-己三烯片段在低波长光照射下可以通过适当的构象进行顺旋而形成6π–电子闭环态,这使二芳基乙烯类化合物具有良好的热稳定性(热不可逆性)、优良的耐疲劳度、高的转化率和量子产率、快的响应速度和出色的固相反应活性,众多优点使得关于二芳基乙烯类光致变色材料的研究异常活跃,并且在超高密度光信息存储、光控分子导线、分子逻辑设备及光驱动器件等光电领域展现出广泛的应用前景和旺盛的生命力。
虽然关于二噻吩乙烯类化合物光致变色性能的研究已经取得巨大进展,但是仍然存在一些问题亟待解决以适应实际应用需要。其中一个亟需但是研究很不充分的性能就是离子调控分子开关光谱性能,而该性能在显示和记忆存储领域是必不可少的。离子调控分子开关光谱性能是指通过加入某种或某类离子来改变分子开关的既有的光致变色性质,从而引起颜色和\或荧光的改变。通过加入离子络合来调控光致变色性能的报道仍然很少(W.H.Zhu,et al.,Chem.Commun.,2012,48,528-530;Q.Zou,et al.,Dyes Pigm.,2014,111,1-7)。相对于加热或者发生化学反应(M.Irie,et al.,J.Am.Chem.Soc.,1994,116,9894-9900;N.R.Branda,et al.,Chem.Commun.,2011,47,10954-10956),离子络合具有更大的应用前景。这是由于在体系中加入离子更便于操作且价格低廉,同时通过加入更强的络合剂可以除去离子从而恢复化合物对光的基本响应,利于体系重复使用。因此,开发具有离子调控分子开关光谱性能、结构和制备工艺简单的低成本有机光致变色材料对发展多寻址光电分子开关、分子导线元件、光致变色发光器件等及其应用具有重大的现实意义。
发明内容
针对现有技术中的上述技术问题,本发明提供了一种基于二芳基乙烯的有机光致变色材料及其制备方法和应用,所述的这种基于二芳基乙烯的有机光致变色材料及其制备方法和应用可以解决现有技术中的有机光致变色材料合成路线复杂、成本较高的技术问题,同时可以解决离子门控分子开关光谱性能欠缺的技术问题。
本发明提供了一种基于二芳基乙烯的有机光致变色材料,其结构式如通式I所示,
其中,X为Cl、Br、I。
本发明还提供了上述的有机光致变色材料的制备方法,在一个反应容器中,依次加入取代的基于二芳基乙烯的单醛类化合物,氯化三氨基胍盐,甲醇或乙醇或四氢呋喃或甲苯,水,所述的取代的基于二芳基乙烯的单醛类化合物,氯化三氨基胍盐,甲醇或乙醇或四氢呋喃或甲苯,水的摩尔体积比为3.0~6.0mmol:1.0~2.0mmol:15~60mL:5~20mL,所述的取代的基于二芳基乙烯的单醛类化合物如通式(II)所示,X为Cl、Br、I,然后于20℃至回流温度下,反应1-24小时,冷却后,过滤,滤饼用乙醚洗涤,得到通式(I)所述的希夫碱类化合物,其反应方程式如下所示,
本发明还提供了上述基于二芳基乙烯的有机光致变色材料在离子调控分子开关光谱性能中的应用。
进一步的,在离子作用下,材料溶液失去光致变色性质,即该溶液在光照环境中无法产生颜色和/或荧光的变化。
进一步的,在铜离子作用下,形成具有通式(III)所示结构的络合物,
从而导致材料专一性地失去光致变色性质,即溶液在紫外和可见光照射下无法产生颜色和/或荧光的变化。
本发明还提供了上述基于二芳基乙烯的有机光致变色材料在制备多寻址光电分子开关、分子导线元件、光致变色发光器件中的应用。
本发明采用的原料可以采用文献常规的方法制备,在此不再赘述。
本发明可以在纯有机溶液(如:四氢呋喃、乙腈、二甲基亚砜、甲醇、乙醇、二氯甲烷)中高选择性地与铜离子作用,作用后溶液颜色发生改变,荧光完全猝灭,实现对铜离子的特异响应。
本发明与铜离子形成的络合物溶液无法实现对紫外和可见光的响应,即失去了基本的光致变色性质,因此,是一类具有离子调控分子开关光谱性能的新型材料。
本发明以基于二芳基乙烯的单醛类化合物和氯化三氨基胍盐形成希夫碱类化合物,其合成方法简单,合成步骤较少、而且原料成本低廉,工艺易于工业化生产,产品提纯高效便捷,所制备的光致变色材料具有高的光转化效率、快速的光响应能力、良好的热稳定性和出色的耐疲劳度。并在离子作用下可以专一性地阻碍材料在光照环境中产生颜色和/或荧光的变化。
本发明所述的具有离子调控分子开关光谱性能的有机光致变色材料具有高的高的光转化效率、快速的光响应能力、良好的热稳定性和出色的耐疲劳度,可作为智能材料应用于光电领域。本发明对于制备多寻址光电分子开关、分子导线元件、光致变色发光器件等方面均具有重要意义。
本发明和已有技术相比,其技术进步是显著的。本发明的制法简捷高效,产率高,经济性好,具有规模化生产的价值,对环境友好。本发明在离子作用下可以专一性地阻碍材料在光照环境中产生颜色和/或荧光的变化,这种离子调控分子开关光谱性能在光电信息领域具有非常重要的作用,可用于制备多寻址光电分子开关、分子导线元件;用于制备光致变色发光器件等。
附图说明
图1是实施例2中,本发明提供的有机光致变色材料C3-DAE的乙腈溶液(10μmol·L-1)在不同光照(365nm单色光源)时间(10s,30s,60s,90s,120s,180s,240s,300s)下的吸收光谱图,横坐标为波长,纵坐标为吸光度。
图2是实施例2中,本发明提供的有机光致变色材料C3-DAE的乙腈溶液(10μmol·L-1)在不同光照(365nm单色光源)时间(10s,30s,60s,90s,120s,180s,240s,300s)下的荧光发射光谱图,横坐标为波长,纵坐标为荧光强度数值。
图3是实施例3中,本发明提供的有机光致变色材料C3-DAE的乙腈溶液(10μmol·L-1)在加入不同浓度Cu2+后的吸收光谱图,Cu2+浓度依次为0、5、10、15、20、25、30、35、40、45、50、55、60、65、70、75、80、85、90μmol·L-1横坐标为波长,纵坐标为吸光度。
具体实施方式
下面通过实施例对本发明作进一步的阐述,其目的仅在于更好地理解本发明的内容。因此,所举之例并不限制本发明的保护范围。
下列实施例中所说的室温是:25-28℃;所用原料及试剂均为市售品或采用文献常规的方法制备。
实施例1(有机光致变色材料C3-DAE的合成):
化合物C3-DAE的合成
1-(5-氯-2-甲基-3-噻吩基)-2-(5-甲酰基-2-甲基-3-噻吩基)环戊烯(化合物1)的制备方法参见文献(H.Tian,et al.,Tetrahedron,2011,67,915-921),氯化三氨基胍盐(化合物2)的制备方法参见文献(H.Krommer,et al.,Chem.Abstr.,1986,104,206730)。
避光状态下,室温下,依次向50mL单口瓶中加入1-(5-氯-2-甲基-3-噻吩基)-2-(5-甲酰基-2-甲基-3-噻吩基)环戊烯(0.882g,2.73mmol)、氯化三氨基胍盐(0.128g,0.912mmol)、15mL乙醇和4mL水,缓慢升温,于回流状态下搅拌4h后,自然冷却至室温,过滤,滤饼用乙醚洗涤,干燥,得0.630g金黄色粉末状固体C3-DAE,产率65.5%。1HNMR(400MHz,CDCl3)δ(ppm):1.88(s,9H),1.95(s,9H),2.05(m,6H),2.74(t,12H),6.58(s,3H),7.05(s,3H),8.60(s,3H).13C NMR(100MHz,CDCl3)δ(ppm):14.2,14.9,18.4,22.8,38.4,38.6,125.4,126.8,133.4,133.4,133.6,134.6,134.9,136.3,140.4,145.2,146.9.HR-ESIMS m/z:[M-Cl-]+calcd.for C49H48N6S6Cl3 +,1017.1330;found,1017.1333.
实施例2(有机光致变色材料C3-DAE的光致变色性能):
将上述所得的化合物C3-DAE溶于乙腈中,配置成浓度为10μmol·L-1的乙腈溶液。在带有搅拌的1cm×1cm×4cm石英比色皿中加入2.5mL的待测溶液,采用365nm单色光源按照不同的时长(10s,30s,60s,90s,120s,180s,240s,300s)对待测溶液进行照射,并采用紫外–可见分光光度计测定吸收光谱,结果如图1所示。在365nm紫外光照射下,吸收光谱于530nm处出现一个新的吸收峰,并且随着时间的延长逐渐增大至达到光稳态,同时溶液颜色也由无色变为粉红色。在可见光(≥550nm)照射下,吸收光谱重新恢复至初始状态并且溶液颜色褪去。以荧光分光光度计研究上述溶液的荧光变化,以357nm作为激发波长,结果如图2所示。可见最大波长位于470nm的荧光发射峰随着光照时间的延长逐渐猝灭。说明该有机发光材料具有典型的光致变色性能。
实施例3(铜离子对有机光致变色材料C3-DAE的光谱性能调控):
将上述所得的化合物C3-DAE溶于乙腈中,配置成浓度为10μmol·L-1的乙腈溶液。在带有搅拌的1cm×1cm×4cm石英比色皿中加入2.5mL的待测溶液,然后用微量注射器分别加入不同浓度的Cu2+(氯化铜)后均匀混合2分钟,测试其吸收光谱,结果如图3所示。随着Cu2 +的不断加入,无色溶液逐渐变为黄色。采用365nm单色光源对该络合物溶液进行长时间照射,不会引起吸收光谱的变化,溶液颜色同样未发生改变。说明化合物C3-DAE的光谱性能可以被Cu2+所调控。
Claims (1)
1.一种基于二芳基乙烯的有机光致变色材料在离子调控分子开关光谱性能中的应用,在铜离子作用下,材料溶液失去光致变色性质,即该溶液在光照环境中无法产生颜色和/或荧光的变化;所述的基于二芳基乙烯的有机光致变色材料的结构式如通式I所示,
其中,X为Cl、Br、I。
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