几种方酸菁染料的NMR及光谱特性研究

doi:10.7517/j.issn.1674-0475.1997.04.314

影像科学与光化学 ›› 1997, Vol. 15 ›› Issue (4): 314-320.DOI: 10.7517/j.issn.1674-0475.1997.04.314

几种方酸菁染料的NMR及光谱特性研究

李毅婷¹, 周金渭², 张复实¹, 王艳乔², 宋心琦¹

1. 清华大学化学系, 北京100084;
2. 中国科学院化学研究所, 北京100080

收稿日期:1997-01-10 修回日期:1997-04-28 出版日期:1997-11-20 发布日期:1997-11-20
通讯作者: 周金渭

NMR AND SPECTROSCOPIC STUDY ON 2,4-BIS(1-ALKYL-3,3-DIMETHYL-2-INDOLINYLIDENEMETHYL)-CYCLOBUTENEDIYLIUM-1,3-DIOLATE DYES

LI Yiting¹, ZHOU Jinwei², ZHANG Fushi¹, WANG Yanqiao², SONG Xinqi¹

1. Department of Chemistry, Tsinghua University, Beijing 100084, P.R. China;
2. Institute of Chemistry, The Chinese Academy of Sciences, Beijing 100080, P.R. China

Received:1997-01-10 Revised:1997-04-28 Online:1997-11-20 Published:1997-11-20

摘要/Abstract

摘要： 研究了几种方酸菁染料的核磁、可见、荧光光谱。通过二维核磁共振谱和¹³CNMR确定了分子的结构和构型。测定了其在不同溶剂中吸收光谱和荧光发射光谱及其发射的荧光量子产率。发现它具有微弱的正向溶致变色特性,通过光谱特征分析得出整个分子处于平面结构并形成一个长的共轭体系,其激发态和基态的结构相近的结论。同时,讨论了结构对分子电荷分布及相应荧光光谱特征的影响。

关键词: 方酸菁染料, 二维核磁共振谱, 溶致变色性, 荧光光谱, 构象

Abstract: The structural characteristics and solvent effect on the absorption and fluorescence emission spectra of squaraine dyes are studied by their NMR, UV-VIS, and fluorescence spectra. The results indicate that the positive solvatochromism of these compounds are not obvious as expected and their structure and configuration in the ground state as well as the excited state are nearly the same. The whole molecule is in a nearly planar form and has a huge conjugate system. The relationships between molecular structure and charge distribution in the molecule, emission spectral feature are analyzed.

Key words: squaraine dye, correlated spectroscopy, solvatochromism, fluorescence spectra, configuration

李毅婷, 周金渭, 张复实, 王艳乔, 宋心琦. 几种方酸菁染料的NMR及光谱特性研究[J]. 影像科学与光化学, 1997, 15(4): 314-320.

LI Yiting, ZHOU Jinwei, ZHANG Fushi, WANG Yanqiao, SONG Xinqi. NMR AND SPECTROSCOPIC STUDY ON 2,4-BIS(1-ALKYL-3,3-DIMETHYL-2-INDOLINYLIDENEMETHYL)-CYCLOBUTENEDIYLIUM-1,3-DIOLATE DYES[J]. Imaging Science and Photochemistry, 1997, 15(4): 314-320.

参考文献

1 (a)Law K Y.Efects of fabrication and agingin the xerographic properties of squaraine photoreceptor devices.J.Imaging Sci.,1987,31:83～87;(b)Tam A C,Balanson R D.Optoacoustic determination of photocarier gen-eration eficiencies of dye films.Appl.Phys.Let.,1980,(37):978～981
2 (a)Loutfy R O,Hsiao C K,Kazmaier P M.Photo conductivity of organic particle dispersions:squaraine dyes.Photogr.Sci.Eng.,1983,27:5～9;(b)Morel D L,Stogryn E L,Ghosh A K,et al.Organic photo voltaic celcorelation between celperformance and molecular structure.J.Phys.Chem.,1984,88:293～298
3 Jipson V P,Jones C R.Infrared dyes for optical storage condensation products of squaric acid and tertiary aromaticamines.J.Vac.Sci.Technol.,1981,18:105～109
4 Law K Y.Squaraine chemistry.Efects of structural change sonthe absorption and multiple fluore scence emission of bis[4-dimethylamino)phenyl]squaraine and its derivatives.J.Phys Chem.,1987,91:5184～5193
5 Law K Y.Squaraine chemstry.A study of the solute-solvent complexation of squaraine in solvents by proton NMR spectroscopy.J.Phys.Chem.,1989,93:5925～5930
6 Sprenger H E,Ziegenbpin W.Condensation products of squaric acid and tertiary aromaticamines.An gew.Chem.,Int.Ed.Engl.,1966,5:894
7 Sprenger H E,Ziegenbpin W.The cyclobutenediylium cation,a novel chromophore from squaric acid.Angew.Chem.,Int.Ed.Engl.,1967,6:553～554
8 Kobayashi Y,Goto M,Kurahashi M.The crystal structure of a squaryliumdye,2,4-bis(1,3,3-trimethyl-2-in-dolinylidenemethyl)cyclobutenediylium-1,3-diolate.Bul.Chem.Soc.Jpn.,1986,(59):311～312
9 Guglielmeti R.In:DürH,Bouas-Laubent,eds.Photochromism,Molecules and Systems.Amsterdam:Elsevier,1990.362
10 Reichart C.In:Solvent and Solvent Effects in Organic Chemistry.Chap.6,2nd ed.Weinheim:VCH,1988
11 Reichart C.In:Solvent and Solvent Effects in Organic Chemistry.Chap.7,2nd ed.Weinheim:VCH,1988
12 Zhou J W,Li Y T,Tang Y W,et al.Detailed investigation on a negative photo chromic spiropyran.J.Pho-tochem.Photobio.,A:Chem.,1995,90:117～123
13 Fabian J,Nakazumi H,Matsuoka M.Near in frared absorbing dyes.Chem.Rev.,1992,92(6):1197～1226
14 Bigelow R W,Freund H-J.An MNDO and CNDO/S(S+DES CI)study on the structrual and electronic proper-ties of a model aquaraine dye and related cyanine.Chem.Phys.,1986,107:159～174

[1]	崔丽霞, 张红红, 李苗, 张彩红, 张国梅, 双少敏, 董川. pH比率荧光探针的制备及光谱研究[J]. 影像科学与光化学, 2018, 36(3): 283-290.
[2]	邓秋, 黎幼群, 唐世华. 纳米ZnS与明胶蛋白质的相互作用[J]. 影像科学与光化学, 2016, 34(4): 336-345.
[3]	李迎迎, 李嫕. 荧光猝灭研究芳醚树枝形聚合物构象[J]. 影像科学与光化学, 2016, 34(2): 144-151.
[4]	王白杨, 肖新光, 唐世华, 刘岑. 明胶/Fe₂S₃纳米生物复合物形成反应的热力学及明胶构象变化[J]. 影像科学与光化学, 2014, 32(6): 505-513.
[5]	潘月礼, 刘会军, 韦文美, 赵祖志. 4-[4-((4-吡啶基)乙烯基)苯乙烯基]-N,N-二正丁基苯胺的合成及光电性质研究[J]. 影像科学与光化学, 2013, 31(1): 33-41.
[6]	陈秀英, 郭琳, 贾显林, 高海燕, 郑昌戈. 新型中位取代七甲川菁染料的合成及光稳定性研究[J]. 影像科学与光化学, 2012, (5): 375-383.
[7]	吴世康, 汪鹏飞. 激子的分裂与高效太阳能电池[J]. 影像科学与光化学, 2011, 29(1): 1-10.
[8]	李明, 曾毅, 李迎迎, 李嫕. 荧光标记聚苯乙烯微球的激光捕获及其原位稳态和时间分辨荧光光谱研究[J]. 影像科学与光化学, 2010, 28(6): 416-424.
[9]	袁钊, 曾毅, 陈金平, 李迎迎, 韩永滨, 李嫕. 以尼罗红为探针对新型两亲性树枝形聚合物微环境的研究[J]. 影像科学与光化学, 2010, 28(5): 343-353.
[10]	俞天智, 丁宪生, 赵玉玲, 钱隆, 范多旺. 开链冠醚Schiff碱配体与过渡金属离子相互作用研究[J]. 影像科学与光化学, 2008, 26(2): 109-115.
[11]	薛金萍, 李文, 于海燕, 洪湖铭, 孙瑞卿, 陈耐生, 黄金陵. 四-α(β)-(4-吡啶氧基)酞菁锌的光物理性质研究[J]. 影像科学与光化学, 2006, 24(4): 262-269.
[12]	洪心进, 罗倩, 王春祥, 薛敏钊, 张青, 盛巧蓉, 刘燕刚. 可溶性的含羧基苝酰亚胺类化合物的合成及其光谱性质研究[J]. 影像科学与光化学, 2006, 24(3): 167-172.
[13]	李贵珍, 蒲守智, 徐景坤, 申亮, 肖强, 陈兵, 赵继全. 光致变色全氟环戊烯类二芳烯化合物的合成及其性质研究[J]. 影像科学与光化学, 2005, 23(3): 167-174.
[14]	肖子丹, 张朝平, 申德君. 氨基酸-银反应的光化学特点[J]. 影像科学与光化学, 2005, 23(3): 209-217.
[15]	唐世华. 同步荧光光谱法研究明胶蛋白质与铜 (Ⅱ)的相互作用[J]. 影像科学与光化学, 2005, 23(2): 102-107.

几种方酸菁染料的NMR及光谱特性研究

NMR AND SPECTROSCOPIC STUDY ON 2,4-BIS(1-ALKYL-3,3-DIMETHYL-2-INDOLINYLIDENEMETHYL)-CYCLOBUTENEDIYLIUM-1,3-DIOLATE DYES

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价