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Physical Vapor Deposited Films of a Perylene Derivative: Supramolecular Arrangement and Thermal Stability
摘要： The analysis of supramolecular arrangement is essential to understand the role of this key factor on the optical and electrical properties of organic thin films. In this work, thin solid films of bis(phenethylimido) perylene (PhPTCD) fabricated using physical vapor deposition (PVD) technique (thermal evaporation), deposited simultaneously onto different substrates (Ag mirror, Ge, and quartz plates) contingent on the characterization technique. The main objective is to study the PhPTCD supramolecular arrangement and the thermal stability of this arrangement in PVD films. The ultraviolet-visible absorption reveals a controlled growth of the PVD films, and the micro-Raman scattering data show that the PhPTCD molecule is not thermally degraded in the conditions of these experiments. The microscopy also shows a homogeneous morphological surface of the PVD film at macro and micro scales, with molecular aggregates at nanoscale. Besides, the PVD film roughness does not follow substrate roughness. The X-ray diffraction indicates a crystalline structure for PhPTCD powder and an amorphous form for PhPTCD PVD film. The infrared absorption spectroscopy points to a preferential flat-on organization of the molecules in the PVD films. In addition, the annealing process (200 oC for 20 minutes) does not affect the supramolecular arrangement of the PhPTCD PVD films.
关键词： perylene,PVD nanostructured films,thermal treatment,supramolecular arrangement
更新于2025-09-09 09:28:46
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Photoluminescent properties in perylene PVD films: Influence of molecular aggregates and supramolecular arrangement
摘要： Organic thin films are at the forefront of basic studies and applications in the field of physics, chemistry, biochemistry and materials science. For example, the intrinsic supramolecular arrangement, or simply the formation of aggregates may alter the optical and electrical properties, which would impact the potential applications of the material. Here, an attempt is made to correlate the molecular structures of two perylene derivatives, bis butylimido perylene (BuPTCD) and bis phenethylimido perylene (PhPTCD), with their film formation, in particular, the supramolecular arrangement and the photoluminescent properties. Emission spectra show that the PhPTCD has a radiative efficiency (RE) higher than that for BuPTCD when both are in solutions (monomers). Complementary, regarding PVD films, UV-Vis absorption measurements reveal that PhPTCD forms, predominantly, J aggregates, which are responsible for perylene derivative emission. However, BuPTCD PVD films are found to provide higher RE than PhPTCD PVD film. This apparent controversy could be explained considering other features such as crystallinity and molecular organization. The PVD film of BuPTCD is crystalline while PhPTCD PVD film is amorphous; BuPTCD has an edge-on while PhPTCD has a face-on molecular organization in PVD films.
关键词： perylene derivatives,PVD thin films,aggregates,photoluminescent properties,supramolecular arrangement
更新于2025-09-09 09:28:46
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Perylene-Based Fluorescent Nanoprobe for Acid-Enhanced Detection of Formaldehyde in Lysosome
摘要： Formaldehyde (FA), as a reactive carbonyl species, is extremely hazardous to human health if its concentration is above normal level. In live cells, lysosome is a main organelle to generate endogenous FA. Thus, the design of facile, stable and sensitive probes for the detection of FA in lysosome is essential. Herein, a self-assembled fluorescent nanoprobe based on homoallylamino substituted perylene (P-FA) has been developed for FA detection in lysosome. P-FA can react with FA along with emission color change from blue to green. P-FA exhibited high sensitivity and selectivity to FA in DMSO solution. In aqueous solution, P-FA self-assembled into uniform sphere-like nanoparticle as a fluorescent nanoprobe. Furthermore, the reaction between the nanoprobe and FA was greatly facilitated at pH 4-5, leading to a lower detection limit (0.96 μM at pH 5) than that in DMSO. In live cells, P-FA nanoprobe achieved long-term tracking of lysosome (over 12 h). The fluorescent nanoprobe was then used for both exogenous and endogenous FA detection. Our work provides a facile and effective strategy for the detection of FA in lysosome.
关键词： Weak Acidity,Perylene,Formaldehyde Detection,Lysosome,Fluorescent Nanoprobe
更新于2025-09-04 15:30:14
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Fabrication of Perylene Tetracarboxylic Diimide-Graphitic Carbon Nitride Heterojunction Photocatalyst for Efficient Degradation of Aqueous Organic Pollutants
摘要： Metal-free g-C3N4 is the promising candidate for the next generation visible light-responsive photocatalyst, however, high recombination probability of the photogenerated charge carriers on g-C3N4 limits its photocatalytic activity. To further increase the intrinsic photocatalytic activity of g-C3N4, here perylene tetracarboxylic diimide-g-C3N4 heterojunctions (PDI/GCN) are prepared by one-step imidization reaction between perylene tetracarboxylic dianhydride (PTCDA) and g-C3N4 in aqueous solution. By the combination of various testing results it is confirmed that the surface hybridization of PTCDA and g-C3N4 in the PDI/GCN heterojunctions via O=C?N?C=O covalent bonds occurs at lower PTCDA-to-g-C3N4 weight percentage. By selecting p-nitrophenol and levofloxacin as the target organic pollutants, the visible light photocatalytic performance of the PDI/GCN heterojunctions are studied. It shows that the PDI/GCN heterojunction prepared at PTCDA-to-g-C3N4 weight percentage of 1% exhibits remarkably higher visible light photocatalytic degradation and mineralization ability towards aqueous target pollutants as compared with g-C3N4 and Degussa P25 TiO2. On the basis of the experimental results including photoelectrochemistry, indirect chemical probe and electron spin resonance spectroscopy it is verified that the surface hybridization in the heterojunctions is responsible for this enhanced photocatalytic activity via accelerating the migration and separation of the photogenerated charge carriers, causing to produce more active species like ?O2?, hVB+ and ?OH for deep oxidation of PNP or LEV to CO2 and inorganic anions.
关键词： graphitic carbon nitride,heterojunction,perylene tetracarboxylic diimide,visible light photocatalysis,organic pollutant
更新于2025-09-04 15:30:14
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Electron/Energy Transfer Studies on Hybrid Materials Based on Dinuclear Coordination Compounds of Twisted Perylene Diimide
摘要： To understand the influence of transition metal ion coordination on the properties and performance of the triads, the symmetric bridging ligand, 1,10-phenanthroline-perylene diimide-1,10-phenanthroline, 1,10-Phen-PDI-1,10-Phen (1) comprising four electron-donating 4-methoxyphenoxy bulky groups at bay-positions and its corresponding square-planar coordination compounds with dichloroplatinum(II), [{PtCl2}2-1] (2) and palladium(II) [{PdCl2}2-1] (3) were prepared in order to tune the photochemical and optical properties of these hybrid materials. These triads show strong electronic absorption bands attributed to the PDI and M(II)(1,10-Phen)Cl2 moieties in DMSO. UV-Vis absorption spectra of compounds were calculated using Time-Dependent Density Functional Theory (TDDFT) for the ground state optimized structures in DCM. Current results indicate that 2 has the lowest HOMO-LUMO gap (2.29 eV in DCM) among the investigated molecules. The energy and charge transfer processes with tailoring molecular structures are one of the important strategies for the design of future functional triads based on donor and acceptor moieties for hybrids optoelectronic devices. Thus, we studied linear absorption, fluorescence, and ultrafast transient absorption spectra measurements for the triads in dichloromethane to investigate the impact of different functionalization strategies on the optical characteristics, photo-stability, and photo-induced charge-transfer (CT) processes. The observed ultrafast intramolecular charge transfer from donor units to acceptor part of 1, 2 and 3 is related to fluorescence quenching and faster singlet state decay on transient absorption measurements. The intramolecular charge transfer mechanism was also compared with the unsymmetrical counterparts that were investigated previously. Symmetrical compounds exhibit faster charge transfer in comparison with the unsymmetrical compounds.
关键词： density functional theory,coordination compounds,ultrafast pump-probe,Perylene diimide,hybrid materials
更新于2025-09-04 15:30:14
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Discrete Dimers of Redox-Active and Fluorescent Perylene Diimide-Based Rigid Isosceles Triangles in the Solid State
摘要： The development of rigid covalent chiroptical organic materials, with multiple, readily available redox states, which exhibit high photoluminescence is of particular importance in relation to both organic electronics and photonics. The chemically stable, thermally robust and redox-active perylene diimide (PDI) fluorophores have received ever-increasing attention owing to their excellent fluorescence quantum yields in solution. Planar PDI derivatives, however, generally suffer from aggregation-caused emission quenching in the solid state. Herein, we report on the design and synthesis of two chiral isosceles triangles wherein one PDI fluorophore and two pyromellitic diimide (PMDI) or naphthalene diimide (NDI) units are arranged in a rigid cyclic triangular geometry. The optical, electronic and magnetic properties of the rigid isosceles triangles are fully characterized by a combination of optical spectroscopies, X-ray diffraction, cyclic voltammetry, and computational modeling techniques. Single-crystal X-ray diffraction analysis shows that both isosceles triangles form discrete, nearly cofacial PDI-PDI π-dimers in the solid state. While the triangles exhibit fluorescence quantum yields of almost unity in solution, the dimers in the solid state exhibit very weak — yet at least an order of magnitude higher — excimer fluorescence yield in comparison with the almost completely quenched fluorescence of a reference PDI. The triangle containing both NDI and PDI subunits shows superior intramolecular energy transfer from the lowest excited singlet state of the NDI to that of the PDI subunit. Cyclic voltammetry suggests that both isosceles triangles exhibit multiple, easily accessible and reversible redox states. Applications beckon in arenas related to molecular optoelectronic devices.
关键词： intramolecular energy transfer,isosceles triangles,rigid covalent chiroptical organic materials,naphthalene diimide,excimer fluorescence,redox-active,π-dimers,photoluminescence,perylene diimide,pyromellitic diimide,cyclic voltammetry
更新于2025-09-04 15:30:14