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61.
Synthesis of a Naphthalimide Functionalized Calix[4]arene; A Host Type Fluorophore for Inclusion Compounds in Organic Medium 总被引:1,自引:0,他引:1
Izilda?A.?Bagatin Alexandre?T.?Cruz Henrique?E.?Toma Mário?J.?Politi Grégoire?J.?-F.?DemetsEmail author 《Journal of inclusion phenomena and macrocyclic chemistry》2005,52(3-4):189-193
This article reports the synthesis and the properties of 5,11,17,23-tetra(t-butyl)-25,27-bis-(ethoxy-1,8-naphthalimide)-26,28-hidroxy-calix[4]arene and the formation of an inclusion compound in organic medium. This functionalized calix[4]arene was conceived as the association of a potential host species with a good fluorophore for optical sensoring purposes. Calix[4]-NI as we will call it, maintains its ‘cone-pinched’ configuration and exhibits typical naphthalimide fluorescence bands in non-polar solvents. Its ability to interact with guest species via hydrogen bonding in its endo-hydrophilic cavity to form inclusion compounds was verified with absorption and fluorescence measurements using N-ethanol-1,8-naphthalimide as guest species, which was projected to fit exactly the host cavity and to interact with its naphthalimide π electrons. For this reason, it was possible to follow the formation of the inclusion compound with electronic spectroscopy.in final form: 17 November 2004.This revised version was published online in July 2005 with a corrected issue number. 相似文献
62.
The photophysical characteristics of a polymerizable 1,8‐naphthalimide dye and its copolymer with styrene have been investigated. The functional properties of both low and high molecular weight fluorophores in the presence of different metal cations have been discussed with regard to their potential application as fluorosensors for the metal cations and protons. In acetonitrile solution the monomeric 1,8‐naphthalimide enhances its fluorescence emission in the presence of metal cations (Zn2+, Fe3+, Co2+, Pb2+, Cu2+, Ni2+, and Mn2+). In aqueous media the poly(St‐co‐MD) exhibits a selective response to Fe3+ cations. The monomeric and polymeric fluorophores also exhibit a considerable increase in their fluorescence intensity at acidic pH values (pH < 6) which suggest that they could be used as ON–OFF probes in analytical devices for signaling the presence of protons. Copyright © 2008 John Wiley & Sons, Ltd. 相似文献
63.
通过在4位引入不同芳香基团,采用Suzuki和Stille偶联反应,设计与合成了一系列新型1,8-萘酰亚胺类荧光染料,并研究了它们的紫外-可见吸收、荧光发射和电化学行为等光物理性质。这些化合物在甲苯中均发射蓝色荧光,最大吸收和荧光发射峰分别在357~378和423~451nm之间,且随着芳香基团供电性增强,吸收和荧光发射波长发生红移。芳香基团的结构对化合物的发光效率影响很大,其中,取代基为甲氧基苯的化合物具有最高的荧光量子效率,可达0.98,而取代基为噻吩的化合物荧光量子效率最低,只有0.17。电化学循环伏安研究表明该类化合物具有较高的电子亲合力,不同芳香基团的引入只影响化合物的被占分子轨道(HOMO)能级,而对化合物的最低空分子轨道(LUMO)能级没有影响,即LUMO能级由1,8-萘酰亚胺单元决定。 相似文献
64.
近年来萘酰亚胺类化合物作为超分子体系中的功能单元逐渐引起了人们的重视,如快速响应的光开关体系[1]、生物荧光探针体系[2]、激光染料天线分子[3]等. 相似文献
65.
WANG Bin WANG Shuai ZHANG Zhen-Xing YANG Pin TIAN Ye WANG Peng ZHANG Qi BAI Gang 《结构化学》2009,28(8):1008-1012
A novel alkynyl substituted N-aryl-1,8-naphthalimide II (C20H11NO2) was synthesized for the discovery and evaluation of new fluorescence probes, and was characterized by X-ray crystal diffraction. It crystallizes in monoclinic, space group P21/n with a = 15.898(3), b = 5.0102(10), c = 17.962(4)A, β = 92.97(3)°, V = 1428.7(5) A^3, Z = 4, Mr = 297.30, Dc = 1.382 g/cm^3, F(000) = 616,/J = 0.090 mm^-1, S = 1.011, the final R = 0.0542 and wR = 0.1204 for 1669 observed reflections with I 〉 2σ(I) and 212 variable parameters. Hydrogen-bounding and n-stacking interactions were discussed. The influence of acetylene group on the fluorescence properties was also investigated. In comparison with N-phenyl-1,8-naphthalimide I (C18H11NO2), few new structure characters and fluorescence properties of the title compound have been found. 相似文献
66.
Eduardo Rezende Triboni Julio Cesar Artur Pedro Berci Filho Iolanda Midea Cuccovia Mario José Politi 《Journal of Physical Organic Chemistry》2009,22(7):703-708
The second‐order rate constants of thiolysis by n‐heptanethiol on 4‐nitro‐N‐n‐butyl‐1,8‐naphthalimide (4NBN) are strongly affected by the water–methanol binary mixture composition reaching its maximum at around 50% mole fraction. In parallel solvent effects on 4NBN absorption molar extinction coefficient also shows a maximum at this composition region. From the spectroscopic study of reactant and product and the known H‐bond capacity of the mixture a rationalization that involves specific solvent H‐donor interaction with the nitro group is proposed to explain the kinetic data. Present findings also show a convenient methodology to obtain strongly fluorescent imides, valuable for peptide and analogs labeling as well as for thio‐naphthalimide derivatives preparations. Copyright © 2008 John Wiley & Sons, Ltd. 相似文献
67.
A Naphthalimide‐Based Cd2+ Fluorescent Probe with Carbamoylmethyl Groups Working as Chelators and PET‐Promoters under Neutral Conditions 下载免费PDF全文
Dr. Koji Tsukamoto Shota Shimabukuro Dr. Miyuki Mabuchi Prof. Dr. Hatsuo Maeda 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(25):8579-8585
We have developed a novel naphthalimide‐based Cd2+ fluorescent probe ( 1 ), featuring almost no background response, high sensitivity and selectivity toward Cd2+ through its high association constant [K=(2.10±0.423)×106], and a practical working pH range. Membrane‐permeability was conferred on 1 by replacing the imide and amide substituents with n‐butyl groups, and hence the derivative ( 4 ) has found practical utility on fluorescent imaging of Cd2+ in HeLa cells. Comparison of fluorescent properties between various compounds derived from 1 has demonstrated that the carbamoylmethyl groups in 1 function not only as Cd2+ chelators but also as promoters for photoinduced electron transfer (PET) by lowering the basicity of the two tertiary amino groups. As a result, 1 and 4 exhibited highly practical performance as Cd2+ probes under neutral conditions. 相似文献
68.
Chi-Hua Tung Yen-Ta Lu Wei-Ting Kao Jen-Wei Liu Yi-Hsuan Lai Shinn-Jong Jiang Hao-Ping Chen Tzenge-Lien Shih 《中国化学会会志》2020,67(7):1254-1262
Three novel naphthalimide-based derivatives were synthesized and tested in vitro as anticancer agents. Our previous report of the C4-benzazole 1,8-naphthalimide derivatives showed good inhibition against murine melanoma. We aimed to synthesize more potent agents and found that compound 5 reported in this article behaved 5- to 10-fold potency than our previous best results. The unique structure of compound 5 consisted of a naphthalimide framework in which C4 position was linked with an ethylenediamine group where the amino group was coupled with a 2-piconic acid moiety. Compound 5 exhibited the most potent inhibitory activity toward human DNA topoisomerase II proteins with IC50 value (2.6 ± 0.1 μM) against murine B16F10 melanoma cells among the three target compounds synthesized in this study. In accordance with this finding, the results of molecular docking also revealed that compound 5 has the highest affinity with human DNA topoisomerase II among the selected compounds. Compound 5 , therefore, has high potential for becoming a lead compound. 相似文献
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70.
设计并合成了萘酰亚胺衍生物N-正己基-4-[2-(3-苯基硫脲)-乙氨基]-1,8-萘酰亚胺(HTN),通过NMR和MS表征了其结构。利用荧光光谱法研究了HTN对苦味酸(PA)的识别作用。研究发现,在C2H5OH/H2O (2:1)体系中,HTN荧光强度随PA浓度的增加而大幅度下降。PA浓度在1×10-6~5×10-4 mol·L-1范围内时,猝灭率(I0-I)/I0与[PA]0.5呈线性关系,R2=0.995 5。常见苯系物,如苯胺、苯甲醛、三硝基甲苯、苯酚、苯乙烯、吡啶、对甲苯磺酸、甲苯、硝基苯及氯苯等均不干扰HTN对PA的识别。结果表明,HTN对PA具有较好的选择性和灵敏度。 相似文献