The synthesis and fluorescence properties of novel 1,8-naphthalimide derivatives

被引：6
作者：
Tian, Zhidan [1 ,2 ]
Liu, Yunchang [1 ,2 ]
Tian, Baozhu [1 ,2 ]
Zhang, Jinlong [1 ,2 ]
机构：
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
来源：
RESEARCH ON CHEMICAL INTERMEDIATES | 2015年 / 41卷 / 02期
关键词：
1,8-Naphthalimide; Fischer indole synthesis; Fluorescence; Stokes shift; Electron-donating; Intramolecular charge transfer; CHEMOSENSOR; DESIGN; DYES;
D O I：
10.1007/s11164-013-1261-6
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Three novel 1,8-naphthalimide derivatives containing indole and indoline were synthesized through Fischer indole synthesis, reduction, and alkylation. Two reference dyes with similar structures to the three novel dyes were also prepared. The absorption and fluorescence spectra of these dyes in a variety of solvents were investigated. In addition, fluorescence of these dyes in solid state was also measured. Intramolecular charge transfer was confirmed within the new dyes by virtue of shifts in emission maximum with increasing solvent polarity. Intermolecular close contacts and lateral intermolecular hydrogen bonding interactions between neighboring columns lead to fluorescence wavelength shift, short in the solution and long in the solid state.
引用
收藏
页码：1157 / 1169
页数：13
相关论文
共 28 条
  • [1] Colorimetric 'naked-eye' and fluorescent sensors for anions based on amidourea functionalised 1,8-naphthalimide structures: anion recognition via either deprotonation or hydrogen bonding in DMSO
    Ali, Haslin Dato Paduka
    Kruger, Paul E.
    Gunnlaugsson, Thorfinnur
    [J]. NEW JOURNAL OF CHEMISTRY, 2008, 32 (07) : 1153 - 1161
  • [2] Synthesis and optical properties of NLO chromophores containing an indoline donor and azo linker
    Ashraf, Mohamed
    Teshome, Ayele
    Kay, Andrew J.
    Gainsford, Graeme J.
    Bhuiyan, M. Delower H.
    Asselberghs, Inge
    Clays, Koen
    [J]. DYES AND PIGMENTS, 2012, 95 (03) : 455 - 464
  • [3] Synthesis and photophysical properties of fluorescence sensing ester- and amidoamine-functionalized 1,8-naphthalimides
    Bojinov, Vladimir B.
    Georgiev, Nikolai I.
    Nikolov, Peter S.
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2008, 193 (2-3) : 129 - 138
  • [4] Synthesis and sensor activity of photostable blue emitting 1,8-naphthalimides containing s-triazine UV absorber and HALS fragments
    Bojinova, Vladimir B.
    Panova, Ionka P.
    Simeonov, Danail B.
    Georgiev, Nikolai I.
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2010, 210 (2-3) : 89 - 99
  • [5] Matrix screening of substituted N-aryl-1,8-naphthalimides reveals new dual fluorescent dyes and unusually bright pyridine derivatives
    Cao, H
    Chang, V
    Hernandez, R
    Heagy, MD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) : 4929 - 4934
  • [6] 3-Urea-1,8-naphthalimides are good chemosensors: a highly selective dual colorimetric and fluorescent ICT based anion sensor for fluoride
    Duke, Rebecca M.
    Gunnlaugsson, Thorfinnur
    [J]. TETRAHEDRON LETTERS, 2011, 52 (13) : 1503 - 1505
  • [7] Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors
    Duke, Rebecca M.
    Veale, Emma B.
    Pfeffer, Frederick M.
    Kruger, Paul E.
    Gunnlaugsson, Thorfinnur
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) : 3936 - 3953
  • [8] Design of NIR-Absorbing Simple Asymmetric Squaraine Dyes Carrying Indoline Moieties for Use in Dye-Sensitized Solar Cells with Pt-Free Electrodes
    Funabiki, Kazumasa
    Mase, Hiroyoshi
    Saito, Yasuteru
    Otsuka, Atsuhiro
    Hibino, Atsuhiko
    Tanaka, Nagisa
    Miura, Hidetoshi
    Himori, Yosuke
    Yoshida, Tsukasa
    Kubota, Yasuhiro
    Matsui, Masaki
    [J]. ORGANIC LETTERS, 2012, 14 (05) : 1246 - 1249
  • [9] Design, Synthesis and Photostability of Novel 1,8-naphthalimide PAMAM Light-harvesting Dendrons
    Georgiev, Nikolai I.
    Bojinov, Vladimir B.
    [J]. JOURNAL OF FLUORESCENCE, 2011, 21 (01) : 51 - 63
  • [10] The design, synthesis and photophysical properties of two novel 1,8-naphthalimide fluorescent pH sensors based on PET and ICT
    Georgiev, Nikolai I.
    Bojinov, Vladimir B.
    Nikolov, Peter S.
    [J]. DYES AND PIGMENTS, 2011, 88 (03) : 350 - 357
123