新型萘酰亚胺类荧光染料的合成及其染色应用
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摘要
为研究荧光染料结构与性能之间的关系,以4-溴-1,8-萘二甲酸酐和含不同取代基的邻苯二胺为原料,合成了3种1,8-萘酰亚胺类荧光染料,并对其结构进行表征,同时测定其紫外-可见光漫反射光谱、紫外-可见光吸收光谱及单光子荧光光谱。在基态优化构型基础上,采用时间依赖密度泛函理论计算该类分散染料在二氯甲烷溶剂中的紫外-可见光吸收光谱的吸收波长和单光子荧光光谱的发射波长。实验测试和理论计算结果均表明,随着邻苯二胺上取代基(—H,—CH_3,—OCH_3)供电子能力的增强,染料吸收光谱发生红移的同时荧光强度会减弱。将3种染料应用于涤纶织物染色,对染色织物的荧光性能和色牢度进行比较测试,结果表明染料b的染色性能最佳。
In order to study the relationship between dye chemical structure and its properties,three naphthalimide-based fluorescent dyes were synthesized from 4-bromo-1,8-naphthalic anhydride and different substituted o-phenylenediamine. The structures were characterized,and the UV-Vis diffusion reflectance spectra,UV-Vis absorption spectra and single-photon fluorescent spectra were investigated.The UV-Vis absorption spectra and single-photon fluorescent emission spectra wavelengths based on the optimized structures were obtained by the time-dependent density function theory. The calculated results well agree with the experimental data,where bathochromic shifts of absorption spectra happens and fluorescent intensity decreases with the electron-donating capability( —H,—CH_3,—OCH_3) of the substituents. The fluorescence and fastness properties of dyed polyester fabrics using these three dyes are also determined,and dye b has the best dyeing property.
In order to study the relationship between dye chemical structure and its properties,three naphthalimide-based fluorescent dyes were synthesized from 4-bromo-1,8-naphthalic anhydride and different substituted o-phenylenediamine. The structures were characterized,and the UV-Vis diffusion reflectance spectra,UV-Vis absorption spectra and single-photon fluorescent spectra were investigated.The UV-Vis absorption spectra and single-photon fluorescent emission spectra wavelengths based on the optimized structures were obtained by the time-dependent density function theory. The calculated results well agree with the experimental data,where bathochromic shifts of absorption spectra happens and fluorescent intensity decreases with the electron-donating capability( —H,—CH_3,—OCH_3) of the substituents. The fluorescence and fastness properties of dyed polyester fabrics using these three dyes are also determined,and dye b has the best dyeing property.
引文
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[24]张跃华,张其平,石文艳,等.1,8-萘酰亚胺荧光单体的合成及光谱的量子化学研究[J].发光学报2011,32(5):505-513.ZHANG Yuehua,ZHANG Qiping,SHI Wenyan,et al.Synthesis and quantum chemistry study on fluorescence spectra of three 1,8-naphthalimide monomers[J].Chinese Journal of Luminescence,2011,32(5):505-513.
[25]杨文芳,杨吕军.锦纶织物荧光染料染色的研究[J].印染,2004,30(15):1-3.YANG Wenfang,YANG LUjun.Polyamide dyeing with fluorescent dyes[J].China Dyeing&Finishing,2004,30(15):1-3
[26]QIN Chuanxiang,TANG Rencheng,CHEN Bo,et al.Study on the dyeing properties of hemicyanine dyes:I:acrylic fabrics[J].Fibers and Polymers,2010,11(2):193-198.
[27]MOHAMMADKHODAEI Zinat,MOKHTARI Javad,NOURI Mahdi.Novel anti-bacterial acid dyes derived from naphthalimide:synthesis,characterisation and evaluation of their technical properties on nylon 6[J].Coloration Technology,2010,126(2):81-85.
[28]KIAKHANI Moosa Sadeghi,ARAMI Mokhtar,GHARANJIG Kamaladin.et al,Synthesis and evaluation of a series of novel monoazo disperse dyes derived from N-carboxylic acid-1,8-naphthalimide on poly(ethylene terphthalate)[J].Fibers and Polymers,2009,10(4):446-451.
[29]PARVIZI P,KHOSRAVI A,MORADIAN S,et al.Synthesis and application of some alkali-clearable azo disperse dyes based on naphthalimide derivatives[J].Journal of the Chinese Chemical Society,2009,56(5):1035-1042.
[2]GHARANJIG Kamaladin,ARAMI Mokhtar,BAHRAMI Hajir,et al.Synthesis,spectral properties and application of novel monoazo disperse dyes derived from N-ester-1,8-naphthalimide to polyester[J].Dyes and Pigments,2008,76(3):684-689.
[3]尹辰,樊君,刘恩周,等.油溶性1,8-萘酰亚胺类荧光染料的合成研究[J].精细化工,2011,28(3):289-292.YIN Chen,FAN Jun,LIU Enzhou,et al.Study on the synthesis of fluorescent dyes of oil soluble 1,8-naphthalimides[J].Fine Chemicals,2011,28(3):289-292.
[4]KHOSRAVI A,MORADIAN S,GHARANJIG K,et al.Synthesis and spectroscopic studies of some naphthalimide based disperse azo dyestuffs for the dyeing of polyester fibres[J].Dyes and Pigments,2006,69(1):79-92.
[5]STOLARSKI D.Fluorescent naphthalimide dyes for polyester fibres[J].Fibres&Textiles in Eastern Europe,2009,73(2):91-95.
[6]张大省,周静宜,王建明.节能降耗新型分散染料常压可染聚酯及其纤维[J].纺织学报,2016,37(2):13-20.ZHANG Dasheng,ZHOU Jingyi,WANG Jianming.Polyester fibers dyed with disperse dyes under atmospheric pressure[J].Journal of Textile Research,2016,37(2):13-20.
[7]STANEVA D,GRABCHEV I,BETCHEVA R.Sensor potential of 1,8-naphthalimide and its dyeing ability of cotton fabric[J].Dyes and Pigments,2013,98(1):64-70.
[8]王晓春,闫金龙,张丽平,等.超高分子质量聚乙烯纤维分散染料染色性能[J].纺织学报,2017,38(11):84-90.WANG Xiaochun,YAN Jinlong,ZHANG Liping,et al.Dyeing properties of ultrahigh molecular weight polyethylene fibers with disperse dye[J].Journal of Textile Research,2017,38(11):84-90.
[9]HUANG Jie,WU Di,GE Haojie,et al.Fluorinated1,8-naphthalimides:synthesis,solid structure and properties[J].Chinese Chemical Letters,2014,25(10):1399-1402.
[10]HUANG Xiaomei,FANG Yi,LI Xin,et al.Novel dyes based on naphthalimide moiety as electron acceptor for efficient dye-sensitized solar cells[J].Dyes and Pigments,2011,90(3):297-303
[11]JIANG Wei,TANG Jinan,QI Qi,et al.An experimental and computational study of intramolecular charge transfer:diarylamino derivatives of 7Hbenzimidazo(2,1-a)benz(d,e)isoquinolin-7-ones[J].Dyes and Pigments,2009,80(3):279-286.
[12]GANIN E,MASUNOV A,SIMINEL A,et al.Preparation,characterization,and electronic structure of asymmetric isonaphthalimide:mechanism of dual fluorescence in solid state[J].The Journal of Physical Chemistry C,2013,117(35):18154-18162.
[13]LAURENT Adèle D,ADAMO Carlo,JACQUEMIN D acquemin.Dye chemistry with time-dependent density functional theory[J].Physical Chemistry Chemical Physics,2014,16(28):14334-14356.
[14]崔俐丽,周丹红,李苗苗,红移型Cu(Ⅱ)离子比率荧光探针的光物理性质[J].物理化学学报,2013,29(4):745-753.CUI Lili,ZHOU Danhong,LI Miaomiao.Photophysical properties of a red-shift Cu(II)ratiometric fluorescent chemosensor[J].Acta Phys Chim Sin,2013,29(4):745-753.
[15]石文艳,吕志敏,雷武,等.两种荧光染料的合成及其量子化学研究[J].南京理工大学学报,2011,35(6):867-872.SHI Wenyan,LUZhimin,LEI Wu,et al.Synthesis and quantum chemistry study of two fluorescent dyes[J].Journal of Nanjing University of Science and Technology,2011,35(6):867-872.
[16]周丹红,郑丽,李蒙召,等.蓝移型萘酰亚胺类Cu2+比率荧光探针的发光机理[J].辽宁师范大学学报(自然科学版),2017,40(2):207-214.ZHOU Danhong,ZHENG Li,LI Mengzhao,et al.Luminescence mechanism of the naphthalimide-based Cu2+blue-shift fluorescent probe[J].Journal of Liaoning Normal University(Natural Science Edition),2017,40(2):207-214.
[17]于鹏美,庄亚丽,毕力,等.半花菁荧光染料光稳定性的量子化学计算[J].纺织学报,2016,37(6):83-90.YU Pengmei,ZHUANG Yali,BI Li,et al.Quantum chemistry study on photostability of two hemicyanine fluorescent dyes[J].Journal of Textile Research,2016,37(6):83-90.
[18]庄亚丽,秦传香,陈国强.两种荧光染料的光稳定性研究[J].印染,2013(22):1-6.ZHUANG Yali,QIN Chuanxiang,CHEN Guoqiang.The photostability of two fluorescent dyes[J].China Dyeing&Finishing,2013(22):1-6.
[19]CLEMENTI,MILIANI C,VERRI G,et al.Application of the kubelka-munk correction for selfabsorption of fluorescence emission in carmine lake paint layers[J].Applied Spectroscopy,2009,63(12):1323-1330.
[20]NARANG Upvan,ZHAO Chan F,BHAWALKAR Jayant D,et al.Characterization of a new solventsensitive two-photon-induced fluorescent(aminostyryl)pyridinium salt dye[J].The Journal of Physical Chemistry,1996,100(11):4521-4525.
[21]QIN Chuanxiang,ZHANG Weizhou,WANG Zhiming,et al.Optical properties of stilbene-type dyes containing various terminal donor and acceptor groups[J].Optical Materials,2008,30(10):1607-1615.
[22]齐齐,孙岳明,哈涌泉.1,8-萘酰亚胺类衍生物的结构及紫外-可见吸收光谱[J].物理化学学报,2009,25(6):1143-1148.QI Qi,SUN Yueming,HA Yongquan.Structures and UV-Vis absorption spectra of 1,8-naphthalimide derivatives[J].Acta Phys Chim Sin,2009,25(6):1143-1148.
[23]孟凡华,郭祥峰,贾丽华,等.N-苯基-1,8-萘酰亚胺衍生物的电子结构和光谱性质的理论研究[J].齐齐哈尔大学学报,2014,30(3):5-10.MENG Fanhua,GUO Xiangfeng,JIA Lihua.et al.Theoretical studies on electronic structure and spectroscopic properties of N-phenyl-1,8-naphthalimide derivatives[J].Journal of Qiqihar University,2014,30(3):5-10.
[24]张跃华,张其平,石文艳,等.1,8-萘酰亚胺荧光单体的合成及光谱的量子化学研究[J].发光学报2011,32(5):505-513.ZHANG Yuehua,ZHANG Qiping,SHI Wenyan,et al.Synthesis and quantum chemistry study on fluorescence spectra of three 1,8-naphthalimide monomers[J].Chinese Journal of Luminescence,2011,32(5):505-513.
[25]杨文芳,杨吕军.锦纶织物荧光染料染色的研究[J].印染,2004,30(15):1-3.YANG Wenfang,YANG LUjun.Polyamide dyeing with fluorescent dyes[J].China Dyeing&Finishing,2004,30(15):1-3
[26]QIN Chuanxiang,TANG Rencheng,CHEN Bo,et al.Study on the dyeing properties of hemicyanine dyes:I:acrylic fabrics[J].Fibers and Polymers,2010,11(2):193-198.
[27]MOHAMMADKHODAEI Zinat,MOKHTARI Javad,NOURI Mahdi.Novel anti-bacterial acid dyes derived from naphthalimide:synthesis,characterisation and evaluation of their technical properties on nylon 6[J].Coloration Technology,2010,126(2):81-85.
[28]KIAKHANI Moosa Sadeghi,ARAMI Mokhtar,GHARANJIG Kamaladin.et al,Synthesis and evaluation of a series of novel monoazo disperse dyes derived from N-carboxylic acid-1,8-naphthalimide on poly(ethylene terphthalate)[J].Fibers and Polymers,2009,10(4):446-451.
[29]PARVIZI P,KHOSRAVI A,MORADIAN S,et al.Synthesis and application of some alkali-clearable azo disperse dyes based on naphthalimide derivatives[J].Journal of the Chinese Chemical Society,2009,56(5):1035-1042.