Solvent influence on the photophysical properties of 4-methoxy-N-methyl-1,8-naphthalimide

被引:32
|
作者
Demets, GJF
Triboni, ER
Alvarez, EB
Arantes, GM
Berci, P
Politi, MJ
机构
[1] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, BR-14040901 Ribeirao Preto, SP, Brazil
[2] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil
[3] Univ Sao Paulo, Inst Quim, BR-05599970 Sao Paulo, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
naphthalimide; solvatochromism and spectrophotometric probe; ethanol-water mixtures;
D O I
10.1016/j.saa.2005.05.008
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
4-Methoxy-N-methyl-1,8-naphthalimide (1) exhibits considerable solvatochromism and its UV-vis spectral properties have been studied in several polar/non-polar and protic/aprotic solvents, as well as in ethanol-water mixtures. The results reveal a strong influence of the solvent's polarity and its hydrogen-bond donor (HBD) capability on the photophysical properties of 1. For binary ethnaol/water mixtures, preferential solvation models describe the band shifts in the probe's visible absorption spectrum well, but they fail to describe the correponding shifts of the emission maxima. Pseudolinear approximations between solvent composition and molecule's transition energies, ET, can be used to study the composition of ethanol-water mixtures, simplifying the mathematical treatment for eventual analytical applications. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:220 / 226
页数:7
相关论文
共 50 条
  • [31] Synthesis and electrochemical properties of novel, donor-acceptor pyrrole derivatives with 1,8-naphthalimide units and their polymers
    Ledwon, Przemyslaw
    Brzeczek, Alina
    Pluczyk, Sandra
    Jarosz, Tomasz
    Kuznik, Wojciech
    Walczak, Krzysztof
    Lapkowski, Mieczyslaw
    ELECTROCHIMICA ACTA, 2014, 128 : 420 - 429
  • [32] An orthomanganation route to 2-substituted derivatives of N-methyl-1, 8-naphthalimide
    Nicholson, Brian K.
    Crosby, Paul M.
    Maunsell, Kieran R.
    Wyllie, Megan J.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 716 : 49 - 54
  • [33] Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination
    Fleming, Cassandra L.
    Ashton, Trent D.
    Pfeffer, Frederick M.
    DYES AND PIGMENTS, 2014, 109 : 135 - 143
  • [34] Structural and Solvent Effects on the Spectroscopic Properties of 1, 8-Naphthalimide Derivatives: A Density Functional Study
    Qi, Qi
    Ha, Yongquan
    Sun, Yueming
    INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2011, 111 (10) : 2234 - 2241
  • [35] Synthesis, structural analysis and application of a series of solid-state fluorochromes-aryl hydrazones of 4-hydrazino-N-hexyl-1,8-naphthalimide
    Ivanov, Ivaylo P.
    Dimitrova, Mashenka B.
    Tasheva, Donka N.
    Cheshmedzhieva, Diana V.
    Lozanov, Valentin S.
    Ilieva, Sonia V.
    TETRAHEDRON, 2013, 69 (02) : 712 - 721
  • [36] A new fluorescent and colorimetric sensor for copper(ii) ion detection based on a 4-styryl-1,8-naphthalimide derivative
    Pavlova, Marina A.
    Panchenko, Pavel A.
    Fedorova, Olga A.
    MENDELEEV COMMUNICATIONS, 2024, 34 (03) : 335 - 337
  • [37] Synthesis and Properties of Blue Fluorescent Dyes Based on Diphenylamine by Introducing an Acetylene Linkage Group with Carbazole and 1,8-Naphthalimide
    Kim, Tae-Heon
    Kwon, Su-Hyeon
    Choi, Jae-Hong
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2019, 40 (12) : 1229 - 1232
  • [38] The synthesis of 1,8-naphthalimide groups containing imidazolium salts/ionic liquids using I-, PF6-, TFSI- anions and their photophysical, electrochemical and thermal properties
    Ozdemir, Saliha
    Varlikli, Canan
    Oner, Ilker
    Ocakoglu, Kasim
    Icli, Siddik
    DYES AND PIGMENTS, 2010, 86 (03) : 206 - 216
  • [39] Electron transfer laser flash photolysis between nucleosides and probe triplet N-(2′-hydroxyethyl)-1,8-naphthalimide
    Li, HQ
    Jiang, ZQ
    Wang, X
    Pan, Y
    Wang, F
    Yu, SQ
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2004, 25 (11): : 2134 - 2136
  • [40] Synthesis, Characterization, and Photo-Physical Properties of Dendrimers Modified With 1,8-Naphthalimide Derivatives as Novel Fluorescent pH Sensors
    Dodangeh, Mohammad
    Gharanjig, Kamaladin
    Arami, Mokhtar
    IEEE SENSORS JOURNAL, 2014, 14 (08) : 2889 - 2896