Optical and charge transport properties of N-butyl-1,8-naphthalimide derivatives as organic light-emitting materials: A theoretical study

Sun, Fuyu; Jin, Ruifa

doi:10.1016/j.jlumin.2014.01.011

Cited by 34 publications

(11 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, naphthalimide derivatives with flexible alkyl/aryl moieties have been found to inhibit the growth of the HL‐60 cell line by induction of apoptosis and have the potential to become a novel class of leading compounds with potential apoptosis‐inducing and anti‐tumor activities . Although several studies on the effects of naphthalimide‐based drugs on serum albumin have been reported , the biological effects and molecular mechanisms of the interactions between naphthalimide‐based anti‐tumor drugs (NADs) and protein have not been fully explored. Therefore a comprehensive investigation of the binding characteristics of these kinds of NADs to HSA is imperative and worthwhile.…”

Section: Introductionmentioning

confidence: 99%

Investigations on the interactions between naphthalimide‐based anti‐tumor drugs and human serum albumin by spectroscopic and molecular modeling methods

Cheng

Zou

et al. 2015

Luminescence

View full text Add to dashboard Cite

The interactions between the three kinds of naphthalimide-based anti-tumor drugs (NADA, NADB, NADC) and human serum albumin (HSA) under simulated physiological conditions were investigated by fluorescence spectroscopy, circular dichroism spectroscopy and molecular modeling. The results of the fluorescence quenching spectroscopy showed that the quenching mechanisms for different drugs were static and their affinity was in a descending order of NADA > NADB > NADC. The relative thermodynamic parameters indicated that hydrophobic force was the predominant intermolecular force in the binding of NAD to HSA, while van der Waals interactions and hydrogen bonds could not be ignored. The results of site marker competitive experiment confirmed that the binding site of HSA primarily took place in site I. Furthermore, the molecular modeling study was consistent with these results. The study of circular dichroism spectra demonstrated that the presence of NADs decreased the α-helical content of HSA and induced the change of the secondary structure of HSA.

show abstract

Section: Introductionmentioning

confidence: 99%

Investigations on the interactions between naphthalimide‐based anti‐tumor drugs and human serum albumin by spectroscopic and molecular modeling methods

Cheng

Zou

et al. 2015

Luminescence

View full text Add to dashboard Cite

show abstract

“…In pyrazine containing 3 the annelated aromatics are in perfect coplanarity (C5−N1−C2− C1 179.1(4)°, C6−N2−C3−C4 179.5(4)°). The value of the X−N−X (X = O, C) angle only depends on the type of attached atoms and decreases from 123.89 (18) and 124.55(19)°for oxygen (1) to 113.3(4) and 115.0(4)°for sp 3 and sp 2 nitrogen atoms in 2−4. Interestingly, the bond distances and angles within the heterocycle are not affected by the electronically different substituents, whereas the C-(thiophene)−N bond distance decreases in the order 1 (1.442(3) Å) > 4 (1.413(4) Å) ≈ 2 (1.406(6) Å) > 3 (1.378(5) Å).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Anal. Calcd for C 24 H 18 Synthesis of 2,5-Diferrocenyl-3,4-bis(N,N-dimethylamino)-thiophene (2). A solution of 1 (0.1 g, 0.18 mmol) in 10 mL of ethanol was treated with a solution of 10 equiv of SnCl 2 ·2H 2 O (0.41 g) in 4 mL of concentrated degassed hydrochloric acid.…”

Section: ■ Introductionmentioning

confidence: 99%

Ferrocenes Bridged by Ethylenediamino Thiophene: Varying Charge Transfer Properties in a Series of 3,4-Di-N-substituted 2,5-Diferrocenyl Thiophenes

et al. 2015

View full text Add to dashboard Cite

A series of 3,4-di-N-substituted 2,5-diferrocenyl thiophenes is reported with the aim to explore the electronic interaction between the organometallic termini over their bridging unit. The syntheses of thiophenes 1−4 were implemented on the basis of 2,5-diferrocenyl-3,4-dinitrothiophene (1), which is accessible within a Pd-promoted Suzuki− Miyaura C,C cross-coupling reaction. Reduction of the nitro functionalities and a subsequent methylation or condensation reaction gives 2,5-diferrocenyl-3,4-bis(N, (4) could be synthesized through conversion of 3 in a two-step reduction/methylation reaction. The spectroscopic characterization of 1−4 was complemented by the investigation of their structural properties in the solid state. The latter disclose no significant influence of the electronically different N substituents on the thiophene bond distances and angles in the solid state. UV−vis solvatochromic studies on thiophenes 1 and 3 in 40 different solvents offer a moderate positive solvatochromic shift of the MLCT absorption of 1; however, for pyrazine 3 a slight negative solvatochromism of the appropriate absorption band was observed. The electrochemical studies on thiophenes 1−4 reveal an increasing thermodynamic stability of the mixed-valent species (K C ) in the order 1 < 2 ≈ 3 < 4. In situ UV−vis−NIR spectroelectrochemical examinations verify these observations. Thus, the NIR absorptions of the corresponding mixed-valent species become more intense and less solvatochromic as the electron-donating effect and the extent of the electronic π system of the bridging unit increase. Hence, the electronic coupling between the iron-based redox centers over the thiophene-based core increases in the order 1 < 2 ≈ 3 < 4.

show abstract

“…It is no surprise that the structure had extensively application in the field of biologically relevant ion sensors, laser materials, targeting biomolecules [14][15][16][17][18]. Construction of 4-amino-1,8-naphthalimide derivatives for anion sensing is of considerable interest in recent years.…”

Section: Introductionmentioning

confidence: 99%

Fluorogenic and chromogenic detection of biologically important fluoride anion with schiff-bases containing 4-amino-1,8-naphthalimide unit

Feng

Geng

Wang

et al. 2015

Journal of Luminescence

View full text Add to dashboard Cite

Optical and charge transport properties of N-butyl-1,8-naphthalimide derivatives as organic light-emitting materials: A theoretical study

Cited by 34 publications

References 64 publications

Investigations on the interactions between naphthalimide‐based anti‐tumor drugs and human serum albumin by spectroscopic and molecular modeling methods

Investigations on the interactions between naphthalimide‐based anti‐tumor drugs and human serum albumin by spectroscopic and molecular modeling methods

Ferrocenes Bridged by Ethylenediamino Thiophene: Varying Charge Transfer Properties in a Series of 3,4-Di-N-substituted 2,5-Diferrocenyl Thiophenes

Fluorogenic and chromogenic detection of biologically important fluoride anion with schiff-bases containing 4-amino-1,8-naphthalimide unit

Contact Info

Product

Resources

About