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Consecutive Charging of a Perylene Bisimide Dye by Multistep Low-Energy Solar-Light-Induced Electron Transfer Towards H2 Evolution.

ABSTRACT: A photocatalytic system containing a perylene bisimide (PBI) dye as a photosensitizer anchored to titanium dioxide (TiO2 ) nanoparticles through carboxyl groups was constructed. Under solar-light irradiation in the presence of sacrificial triethanolamine (TEOA) in neutral and basic conditions (pH 8.5), a reaction cascade is initiated in which the PBI molecule first absorbs green light, giving the formation of a stable radical anion (PBI.- ), which in a second step absorbs near-infrared light, forming a stable PBI dianion (PBI2- ). Finally, the dianion absorbs red light and injects an electron into the TiO2 nanoparticle that is coated with platinum co-catalyst for hydrogen evolution. The hydrogen evolution rates (HERs) are as high as 1216 and 1022 μmol h-1 g-1 with simulated sunlight irradiation in neutral and basic conditions, respectively.

SUBMITTER: Xu Y

PROVIDER: S-EPMC7317913 | biostudies-literature |

REPOSITORIES: biostudies-literature

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In Silico Ultrafast Nonlinear Spectroscopy Meets Experiments: The Case of Perylene Bisimide Dye.

Project description:Spectroscopy simulations are of paramount importance for the interpretation of experimental electronic spectra, the disentangling of overlapping spectral features, and the tracing of the microscopic origin of the observed signals. Linear and nonlinear simulations are based on the results drawn from electronic structure calculations that provide the necessary parameterization of the molecular systems probed by light. Here, we investigate the applicability of excited-state properties obtained from linear-response time-dependent density functional theory (TDDFT) in the description of nonlinear spectra by employing the pseudowavefunction approach and compare them with benchmarks from highly accurate RASSCF/RASPT2 calculations and with high temporal resolution experimental results. As a test case, we consider the prediction of femtosecond transient absorption and two-dimensional electronic spectroscopy of a perylene bisimide dye in solution. We find that experimental signals are well reproduced by both theoretical approaches, showing that the computationally cheaper TDDFT can be a suitable option for the simulation of nonlinear spectroscopy of molecular systems that are too large to be treated with higher-level RASSCF/RASPT2 methods.

| S-EPMC8582250 | biostudies-literature

Macrocyclic Donor-Acceptor Dyads Composed of a Perylene Bisimide Dye Surrounded by Oligothiophene Bridges.

Project description:Two macrocyclic architectures comprising oligothiophene strands that connect the imide positions of a perylene bisimide (PBI) dye have been synthesized via a platinum-mediated cross-coupling strategy. The crystal structure of the double bridged PBI reveals all syn-arranged thiophene units that completely enclose the planar PBI chromophore via a 12-membered macrocycle. The target structures were characterized by steady-state UV/Vis absorption, fluorescence and transient absorption spectroscopy, as well as cyclic and differential pulse voltammetry. Both donor-acceptor dyads show ultrafast Förster Resonance Energy Transfer and photoinduced electron transfer, thereby leading to extremely low fluorescence quantum yields even in the lowest polarity cyclohexane solvent.

| S-EPMC9299635 | biostudies-literature

Tetrahydroxy-Perylene Bisimide Embedded in a Zinc Oxide Thin Film as an Electron-Transporting Layer for High-Performance Non-Fullerene Organic Solar Cells.

Project description:By introduction of four hydroxy (HO) groups into the two perylene bisimide (PBI) bay areas, new HO-PBI ligands were obtained which upon deprotonation can complex ZnII ions and photosensitize semiconductive zinc oxide thin films. Such coordination is beneficial for dispersing PBI photosensitizer molecules evenly into metal oxide films to fabricate organic-inorganic hybrid interlayers for organic solar cells. Supported by the photoconductive effect of the ZnO:HO-PBI hybrid interlayers, improved electron collection and transportation is achieved in fullerene and non-fullerene polymer solar cell devices, leading to remarkable power conversion efficiencies of up to 15.95?% for a non-fullerene based organic solar cell.

| S-EPMC6772159 | biostudies-literature

Mechanoresponsive Self-Assembled Perylene Bisimide Films.

Project description:In this work, self-assembled amino-acid appended perylene bisimides (PBIs) have been studied that when processed into thin films change their resistivity in response to being bent. The PBIs assemble into structures in water and form thin films upon drying. These normally delicate thin films can be tolerant to bending, depending on the aggregates they form. Furthermore, the films then reversibly change their resistivity in response to this mechanical stimulus. This change is proportional to the degree of bending of the film giving them the potential to be used quantitatively to measure mechanical movement, such as in wearable devices.

| S-EPMC7522684 | biostudies-literature

Self-sorted Oligophenylvinylene and Perylene Bisimide Hydrogels.

Project description:We describe two component hydrogels with networks composed of self-sorted fibres. The component gelators are based on 1,4-distyrylbenzene (OPV3) and perylene bisimide (PBI) units. Self-sorted gels can be formed by a slow decrease in pH, which leads to sequential assembly. We demonstrate self-sorting by NMR, rheology and small angle X-ray scattering (SAXS). Photoconductive xerogels can be prepared by drying these gels. The wavelength response of the xerogel is different to that of the PBI alone.

| S-EPMC5566499 | biostudies-literature

Differently Linked Perylene Bisimide Dimers with Various Twisting and Phase Structures for Nonfullerene All-Small-Molecule Organic Solar Cells.

Project description:Nonfullerene all-small-molecule organic solar cells (NF all-SMSCs) are an important classification in the organic solar cell system. However, the application and research of NF all-SMSCs are limited due to the easy aggregation of small molecules to form large-phase domains. Perylene bisimides (PBIs) have been widely used as nonfullerene acceptors. Simply changing the link position of the PBI dimer can control the accumulation of molecules to regulate the size of the phase domain. Herein, the bay-linked, ortho-linked, and hydrazine-linked PBI dimers as nonfullerene acceptors, named as B-SdiPBI, O-SdiPBI, and H-SdiPBI, respectively, were chosen. The link position of the PBI dimer can lead to diverse molecular torsion and planarity, which affects the film-forming ability, phase separation, and thus optoelectronic properties. NF all-SMSCs based on B-SdiPBI, O-SdiPBI, and H-SdiPBI as nonfullerene acceptors and a small molecule DR3TBDTT as the donor achieve the best power conversion efficiencies of 1.93, 3.30, and 4.05%, respectively. The result is consistent with the sequence of inter-PBI twist and phase domain size of the corresponding blend films in the device. The DR3TBDTT:H-SdiPBI system has the best efficiency with the largest dihedral angle of H-SdiPBI (ψ = 90°) and an appropriate phase size (10-40 nm), whereas the smaller dihedral angle of O-SdiPBI (ψ = 86°) produces a larger phase size (20-50 nm) and the smallest dihedral angle of B-SdiPBI (ψ = 71°) gives the largest phase size (30-80 nm). This illustrates that the twist angle can effectively increase the phase separation between the acceptor and donor to obtain an effective phase size in this system. The work provides a guide for designing the acceptors and controlling phase domains of high-performance NF all-SMSCs.

| S-EPMC7391947 | biostudies-literature

High-Performance Non-Fullerene Organic Solar Cells Based on a Selenium-Containing Polymer Donor and a Twisted Perylene Bisimide Acceptor.

Project description:A novel polymer donor (PBDTS-Se) is designed to match with a non-fullerene acceptor (SdiPBI-S). The corresponding solar cells show a high efficiency of 8.22%, which result from synergetic improvements of light harvesting, charge carrier transport and collection, and morphology. The results indicate that rational design of novel donor materials is important for non-fullerene organic solar cells.

| S-EPMC5039968 | biostudies-literature

Hydrogen-bonded perylene bisimide J-aggregate aqua material.

Project description:A new twelvefold methoxy-triethyleneglycol-jacketed tetraphenoxy-perylene bisimide (MEG-PBI) amphiphile was synthesized that self-assembles into two types of supramolecular aggregates in water: red-coloured aggregates of low order and with weak exciton coupling among the PBIs and blue-coloured strongly coupled J-aggregates consisting of a highly ordered hydrogen-bonded triple helix of PBIs. At room temperature this PBI is miscible with water at any proportions which enables the development of robust dye aggregates in solution, in hydrogel states and in lyotropic liquid crystalline states. In the presence of 60-95 wt% water, self-standing coloured hydrogels exhibit colour changes from red to blue accompanied by a fluorescence light-up in the far-red region upon heating in the range of 30-50 °C. This phenomenon is triggered by an entropically driven temperature-induced hydrogen-bond-directed slipped stacking arrangement of the MEG-PBI chromophores within structurally well-defined J-aggregates. This versatile aqua material is the first example of a stable PBI J-aggregate in water. We anticipate that this study will open a new avenue for the development of biocompatible functional materials based on self-assembled dyes and inspire the construction of other hydrogen-bonded supramolecular materials in the highly competitive solvent water.

| S-EPMC6124903 | biostudies-other

New fluorescent perylene bisimide indicators--a platform for broadband pH optodes.

Project description:Asymmetric perylene bisimide (PBI) dyes are prepared and are shown to be suitable for the preparation of fluorescence chemosensors for pH. They carry one amino-functional substituent which introduces pH sensitivity via photoinduced electron transfer (PET) while the other one increases solubility. The luminescence quantum yields for the new indicators exceed 75% in the protonated form. The new indicators are non-covalently entrapped in polyurethane hydrogel D4 and poly(hydroxyalkylmethacrylates). Several PET functions including aliphatic and aromatic amino groups were successfully used to tune the dynamic range of the sensor. Because of their virtually identical spectral properties, various PBIs with selected PET functions can easily be integrated into a single sensor with enlarged dynamic range (over 4 pH units). PBIs with two different substitution patterns in the bay position are investigated and possess variable spectral properties. Compared with their tetrachloro analogues, tetra-tert-butyl-substituted PBIs yield more long-wave excitable sensors which feature excellent photostability. Cross-sensitivity to ionic strength was found to be negligible. The practical applicability of the sensors may be compromised by the long response times (especially in case of tetra-tert-butyl-substituted PBIs).

| S-EPMC3100492 | biostudies-literature

Deracemization of Carbohelicenes by a Chiral Perylene Bisimide Cyclophane Template Catalyst.

Project description:Deracemization describes the conversion of a racemic mixture of a chiral molecule into an enantioenriched mixture or an enantiopure compound without structural modifications. Herein, we report an inherently chiral perylene bisimide (PBI) cyclophane whose chiral pocket is capable of transforming a racemic mixture of [5]-helicene into an enantioenriched mixture with an enantiomeric excess of 66 %. UV/Vis and fluorescence titration studies reveal this cyclophane host composed of two helically twisted PBI dyes has high binding affinities for the respective homochiral carbohelicene guests, with outstanding binding constants of up to 3.9×1010 m-1 for [4]-helicene. 2D NMR studies and single-crystal X-ray analysis demonstrate that the observed strong and enantioselective binding of homochiral carbohelicenes and the successful template-catalyzed deracemization of [5]-helicene can be explained by the enzyme-like perfect shape complementarity of the macrocyclic supramolecular host.

| S-EPMC8362091 | biostudies-literature

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