双萘酰亚胺衍生物用于检测水溶液中的苦味酸

设计合成了一个新的双1,8-萘酰亚胺衍生物(Bis-Nph), 并通过核磁共振波谱和高分辨质谱鉴定了其结构. Bis-Nph呈现出典型的分子内电荷转移(ICT)和聚集诱导增强发射(AIEE). 该化合物可以作为荧光探针检测水溶液中的苦味酸(2,4,6-三硝基苯酚, TNP), 检出限为5.8×10^-7 mol/L. 作用机制为TNP的质子转移到Bis-Nph, 有效地阻断了其ICT发射, 使荧光发生显著猝灭. 另外, Bis-Nph的细胞毒性较低, 可做成试纸进行TNP的快速检测.     

A ratiometric near-infrared naphthalimide-based fluorescent probe with high sensitivity for detecting Fe2+ in vivo

Iron is one of the essential trace elements in the human body. It plays an important role in human biology and pathology. Deregulation of iron levels in cells is associated with disease development. In this work, we synthesized a novel near-infrared intramolecular charge transfer (ICT) based ratiometric fluorescent probe to detect Fe²⁺, by using naphthalimide and indole moieties as building blocks. Our work showed that the radiometric probe has excellent selectivity, sensitivity and rapid response. Moreover, we could successfully perform real-time monitoring of Fe²⁺ in HeLa cells and C. elegans.     

The fluorescence of polyamidoamine dendrimers peripherally modified with 1,8-naphthalimide groups: Effect of the rare earth ions and protons

We report the absorption spectra, fluorescent spectra and photophysical properties of G 2.0 polyamidoamine dendrimers with peripheral 1,8-naphthalimide groups with the hydrogen ions, the rare earth ions (Er³⁺, Tb³⁺, Nb³⁺, Eu³⁺, Yb³⁺ and Gd³⁺) and the mixture of the rare earth metal and hydrogen ions. The presence of the rare earth ions and hydrogen ions was found to enhance the fluorescence owing to the coordination between the rare earth metal or hydrogen ions and internal amido groups of polyamidoamine (PAMAM) from dendrimer. The result from the 3D isogram of the fluorescence spectra for the dendrimers with peripheral 1,8-naphthalimide groups show that it was obtained for the different emission fluorescence intensity and scope by varying the excitation wavelength and the different rare earth ions as well as its concentration. The results obtained reveal that the capacities of these systems might have acted as a sensitive label agent of the rare earth cations and protons.     

1,8-萘酰亚胺衍生物的合成、表征及电存储性能

本文以三苯胺结构作为电子给体,与三种接有不同吸电子基团的1,8-萘酐反应合成了具有电子给-受体结构的N-(4-三苯胺)-1,8-萘酰亚胺(NA-ATPA)、N-(4-三苯胺)-(4-氰基)-1,8-萘酰亚胺(NA(CN)-ATPA)和N-(4-三苯胺)-(4-硝基)-1,8-萘酰亚胺(NA(NO_2)-ATPA),并对它们的结构进行了表征。利用紫外可见光谱、荧光发射光谱和循环伏安法对产物的光物理性能和电化学性能进行了测试,并测试了其存储行为,结果显示NA-ATPA表现出易失的静态随机存储行为(SRAM),NACN-ATPA表现出非易失的闪存型存储(Flash),NA(NO_2)-ATPA表现出非易失只读型存储(WORM)。三种萘酰亚胺对存储行为中高导态的维持能力逐渐增强,其原因是引入的吸电子基团的吸电子性越强,其LUMO值和能隙值降低的越多,越利于电荷转移,形成更稳定的电荷转移络合物。另外,本文还对原料和产物的电子结构、分子轨道和能级进行了分子模拟计算,研究了三种化合物基态和激发态的差别,并对其电子转移过程进行了理论分析。     

Ratiometric fluorescent and colorimetric sensors for Cu based on 4,5-disubstituted-1,8-naphthalimide and sensing cyanide via Cu displacement approach

Two 4,5-disubstituted-1,8-naphthalimide derivatives 1 and 2 were synthesized as ratiometric fluorescent and colorimetric sensors for Cu²⁺, respectively. In 100% aqueous solutions of 1, the presence of Cu²⁺ induces a strong and increasing fluorescent emission centered at 478 nm at the expense of the fluorescent emission of 1 centered at 534 nm. Compound 2 senses Cu²⁺ by means of a colorimetric (primrose yellow to pink) method with a thorough quench in emission attributed to the deprotonation of the secondary amine conjugated to the naphthalimide fluorophore. 1-Cu²⁺ and 2-Cu²⁺ sense cyanide in ratiometric way via colorimetric and fluorescent changes.     

Naphthalimide-modified near-infrared cyanine dye with a large stokes shift and its application in bioimaging

A naphthalimide-modifi ed near-infrared cyanine dye (emission at 785 nm) with a large Stokes shift (up to 165 nm) has been synthesized and had favorable lysosome-targeting property.     

1,8‐Naphthalimide: A Potent DNA Intercalator and Target for Cancer Therapy

The poor pharmacokinetics, side effects and particularly the rapid emergence of drug resistance compromise the efficiency of clinically used anticancer drugs. Therefore, the discovery of novel and effective drugs is still an extremely primary mission. Naphthalimide family is one of the highly active anticancer drug based upon effective intercalator with DNA. In this article, we review the discovery and development of 1,8‐naphthalimide moiety, and, especially, pay much attention to the structural modifications and structure activity relationships. The review demonstrates how modulation of the moiety affecting naphthalimide compound for DNA binding that is achieved to afford a profile of antitumor activity. The DNA binding of imide and ring substitution at naphthalimide, bisnaphthalimide, naphthalimide‐metal complexes is achieved by molecular recognition through intercalation mode. Thus, this synthetic/natural small molecule can act as a drug when activation or inhibition of DNA function, is required to cure or control the cancer disease. The present study is a review of the advances in 1,8‐naphthalimide‐related research, with a focus on how such derivatives are intercalated into DNA for their anticancer activities.     

π-Sufficient heteroaromatic compounds fused naphthalimide unit as novel solvatochromic fluorophores

The carbazoles 1 and dibenzofurans 2 having naphthalimide unit were synthesized by the cross coupling reaction of 4-bromonaphthalimide 3 with aniline and phenol derivatives followed by the intramolecular cyclization, respectively. The chromophores 1c and 2c substituted methoxy group exhibited the strong fluorescence solvatochromism.     

Naphthalimide based disperse dyes for nylon 6 and polyester (pet) fibers: Synthesis and evaluation of technical properties in the presence of urea

Technical properties of two naphthalimide based disperse dyes on nylon 6 and polyester fibers were investigated in the presence of urea.The two naphthalimide based disperse dyes were synthesized.The dyes were purified and then fully characterized using ~1H-NMR,FTIR and melting point analysis.Dispersion of the dyes was prepared in water and applied on nylon 6 and PET fibers.The dyes offered good build-up properties on the substrates.In order to increase dye adsorption of the substrates,urea was added into...     

A novel Cr turn-on probe based on naphthalimide and BINOL framework

Naphthalimide and BINOL framework based fluorescent probe NP-B was rationally designed and synthesized. NP-B exhibited ‘turn-on’ fluorescence for Cr³⁺ and high selectivity over other metal ions. 1:1 binding mode between NP-B and Cr³⁺ was proposed and the mode was verified through MALDI-TOF mass spectrum. The detection limit was calculated to be 0.20 μM, which indicated the good sensitivity for Cr³⁺.