通过铃木耦合反应对萘部分具有扩展共轭的1,8-萘二甲酰亚胺的光物理性质进行研究。
Investigation of photophysical properties of 1,8-naphthalimides with an extended conjugation on naphthalene moiety via Suzuki coupling reaction.
作者信息
Jang Eunju, Ding Ting, Xie Meng, Cao Haishi
机构信息
Department of Chemistry, University of Nebraska-Kearney, Kearney, NE, 68849, USA.
出版信息
J Photochem Photobiol A Chem. 2018 Sep 1;364:145-150. doi: 10.1016/j.jphotochem.2018.05.046. Epub 2018 Jun 5.
Abstract
Five 4-substituted 1,8-naphthalimides (-), with an extended conjugation on the naphthalene ring, have been synthesized via Suzuki coupling reaction. These derivatives showed a large Stokes shift (up to 200 nm) and longer emission due to the increase of conjugation. Besides strong solvation effect, the low quantum yield were observed in protic solvents compared to in aprotic solvents. The anion forms of - obtained from reacting with NaH gave a significant red-shift for both absorption and emission spectra. These results provided a new strategy for preparation of fluorescent dyes with a long emission on the basis of 1,8-naphthalimde structure by using Suzuki coupling reaction.
摘要
通过铃木耦合反应合成了五种在萘环上具有扩展共轭的4-取代-1,8-萘二甲酰亚胺（-）。由于共轭的增加，这些衍生物表现出较大的斯托克斯位移（高达200nm）和更长的发射波长。除了强烈的溶剂化效应外，与非质子溶剂相比，在质子溶剂中观察到较低的量子产率。与NaH反应得到的-的阴离子形式在吸收光谱和发射光谱上都有显著的红移。这些结果为基于1,8-萘二甲酰亚胺结构通过铃木耦合反应制备具有长发射的荧光染料提供了一种新策略。
相似文献
1
Investigation of photophysical properties of 1,8-naphthalimides with an extended conjugation on naphthalene moiety via Suzuki coupling reaction.通过铃木耦合反应对萘部分具有扩展共轭的1,8-萘二甲酰亚胺的光物理性质进行研究。
J Photochem Photobiol A Chem. 2018 Sep 1;364:145-150. doi: 10.1016/j.jphotochem.2018.05.046. Epub 2018 Jun 5.
2
Fluorescence behaviour of 2-, 3- and 4-amino-1,8-naphthalimides: effects of the substitution positions of the amino functionality on the photophysical properties.2-、3-和 4-氨基-1,8-萘酰亚胺的荧光行为：氨基官能团取代位置对光物理性质的影响。
Photochem Photobiol Sci. 2018 Oct 10;17(10):1319-1328. doi: 10.1039/c8pp00302e.
3
Solvent-induced multicolour fluorescence of amino-substituted 2,3-naphthalimides studied by fluorescence and transient absorption measurements.通过荧光和瞬态吸收测量研究溶剂诱导的氨基取代的2,3-萘二甲酰亚胺的多色荧光
Photochem Photobiol Sci. 2016 Jul 6;15(7):842-50. doi: 10.1039/c6pp00048g.
4
Synthesis and photophysical characterizations of thermal-stable naphthalene benzimidazoles.萘并苯并咪唑的热稳定性合成及光物理特性研究。
J Fluoresc. 2011 Jul;21(4):1565-73. doi: 10.1007/s10895-011-0845-z. Epub 2011 Jan 29.
5
A comparative study into two dual fluorescent mechanisms via positional isomers of N-hydroxyarene-1,8-naphthalimides.通过N-羟基芳烃-1,8-萘二甲酰亚胺的位置异构体对两种双荧光机制的比较研究。
J Fluoresc. 2009 Jul;19(4):681-91. doi: 10.1007/s10895-009-0462-2. Epub 2009 Feb 4.
6
Synthesis, Photophysical and Redox Properties of the D-π-A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety.含9-苯基-9H-咔唑部分的D-π-A型嘧啶染料的合成、光物理及氧化还原性质
J Fluoresc. 2015 May;25(3):763-75. doi: 10.1007/s10895-015-1565-6. Epub 2015 Mar 31.
7
Distinctive tunable photophysical properties of versatile environmentally-sensitive tribranched cyanopyridine fluorophores.多功能环境敏感三分支氰基吡啶荧光团的独特可调谐光物理性质。
Spectrochim Acta A Mol Biomol Spectrosc. 2021 Mar 5;248:119169. doi: 10.1016/j.saa.2020.119169. Epub 2020 Nov 12.
8
Solvent influence on the photophysical properties of 4-methoxy-N-methyl-1,8-naphthalimide.溶剂对4-甲氧基-N-甲基-1,8-萘二甲酰亚胺光物理性质的影响。
Spectrochim Acta A Mol Biomol Spectrosc. 2006 Jan;63(1):220-6. doi: 10.1016/j.saa.2005.05.008. Epub 2005 Jun 22.
9
Highly solvatochromic fluorescent naphthalimides: design, synthesis, photophysical properties and fluorescence switch-on sensing of ct-DNA.高溶剂变色荧光萘酰亚胺：设计、合成、光物理性质及 ct-DNA 的荧光开启传感。
Bioorg Med Chem Lett. 2013 Jan 1;23(1):96-101. doi: 10.1016/j.bmcl.2012.11.003. Epub 2012 Nov 12.
10
Frontier molecular orbital analysis of dual fluorescent dyes: predicting two-color emission in N-aryl-1,8-naphthalimides.双荧光染料的前沿分子轨道分析：预测 N-芳基-1,8-萘酰亚胺的双色发射。
Org Biomol Chem. 2010 Jul 21;8(14):3195-201. doi: 10.1039/c001912g.
本文引用的文献
1
Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes.杂芳基卤化物的位点选择性铃木-宫浦偶联反应——了解重要药物类别中的趋势
Chem Sci. 2017 Jan 1;8(1):40-62. doi: 10.1039/c6sc02118b. Epub 2016 Aug 9.
2
Investigation of desilylation in the recognition mechanism to fluoride by a 1,8-naphthalimide derivative.1,8-萘二甲酰亚胺衍生物对氟化物识别机制中去硅基化反应的研究。
Org Biomol Chem. 2014 Nov 7;12(41):8275-9. doi: 10.1039/c4ob01500b. Epub 2014 Sep 10.
3
Suzuki-Miyaura cross-coupling reactions of unprotected haloimidazoles.未保护的卤代咪唑的铃木-宫浦交叉偶联反应。
J Org Chem. 2014 Sep 19;79(18):8871-6. doi: 10.1021/jo501326r. Epub 2014 Aug 27.
4
Excimer-monomer switch: a reaction-based approach for selective detection of fluoride.准分子-单体转换：一种基于反应的氟化物选择性检测方法。
Analyst. 2014 Jul 21;139(14):3588-92. doi: 10.1039/c4an00522h.
5
Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents.近年来，1,8-萘酰亚胺基 DNA 靶向结合物、抗癌和荧光细胞成像剂的发展取得了新进展。
Chem Soc Rev. 2013 Feb 21;42(4):1601-18. doi: 10.1039/c2cs35467e. Epub 2013 Jan 17.
6
Palladium-catalyzed alkyne insertion/Suzuki reaction of alkyl iodides.钯催化炔烃插入/Suzuki 反应的碘化烷基。
J Am Chem Soc. 2012 Sep 19;134(37):15297-300. doi: 10.1021/ja307761f. Epub 2012 Sep 7.
7
Synthesis and photochromism of naphthopyrans bearing naphthalimide chromophore: predominant thermal reversibility in color-fading and fluorescence switch.含萘酰亚胺生色团的萘并吡喃的合成及光致变色性：颜色褪色和荧光开关中主要的热可逆性。
J Phys Chem B. 2011 Dec 15;115(49):14648-58. doi: 10.1021/jp208082w. Epub 2011 Nov 11.
8
A naphthalimide fluorophore with efficient intramolecular PET and ICT processes: application in molecular logic.具有高效分子内 PET 和 ICT 过程的萘酰亚胺荧光团：在分子逻辑中的应用。
Org Biomol Chem. 2011 Aug 7;9(15):5436-44. doi: 10.1039/c1ob05481c. Epub 2011 Jun 10.
9
A new prodrug-derived ratiometric fluorescent probe for hypoxia: high selectivity of nitroreductase and imaging in tumor cell.一种新的基于前药的比率荧光探针用于缺氧检测：对硝基还原酶具有高选择性和肿瘤细胞成像。
Org Lett. 2011 Mar 4;13(5):928-31. doi: 10.1021/ol102975t. Epub 2011 Jan 26.
10
Dual fluorescent N-aryl-2,3- naphthalimides: applications in ratiometric DNA detection and white organic light-emitting devices.双荧光 N-芳基-2,3-萘酰亚胺：在比率型 DNA 检测和白色有机发光器件中的应用。
Org Lett. 2010 Nov 5;12(21):4796-9. doi: 10.1021/ol101760m.
Zotero 插件