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Book ChapterDOI

Synthesis and Characterization of Bay Substituted Perylene Diimide Small Molecule for Organic Solar Cell Application

TL;DR: In this article, the synthesis of N,N′-Bis(hexyl)-1,7-di(thiophenyl)perylene -3,4:9,10-tetracarboxylic acid diimide (T-PDI-H) based small molecule was confirmed by FT-IR and NMR techniques.
Abstract: We report the synthesis of N,N′-Bis(hexyl)-1,7-di(thiophenyl)perylene -3,4:9,10-tetracarboxylic acid diimide (T-PDI-H) based small molecule by Suzuki coupling method for organic photovoltaic (OPV) application. The synthesized small molecule was confirmed by FT-IR and NMR techniques. The T-PDI-H showed broad and strong absorption in the UV-Visible region. From UV-Visible spectra we observed a low optical band gap (E g opt ) of 1.96 eV for T-PDI-H. From the cyclic voltammetry, the calculated HOMO, LUMO and electrochemical band gap (E g ele ) for the small molecule was −5.77, −3.44 and 2.33 eV respectively. Thermogravimetric analysis was employed to elucidate the thermal stability of T-PDI-H small molecule, it showed good thermal stability up to 400 °C. The preferred property for the high power conversion efficiency (PCE) OPV device, molecule must possess broad and strong absorption in the UV-Vis region, low band gap , and high thermal and environmental stability. T-PDI-H small molecule might satisfy the above standards with the chance to give maximum power conversion efficiency (PCE).
Citations
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Journal ArticleDOI
03 Dec 2020-Polymers
TL;DR: Photoluminescence quenching of up to 82% was observed in solution blends of the G1PPT-co-PEDOT star copolymer and N,N′-diisopropyl naphthalene diimide (NDI), which demonstrates the occurrence of photoinduced intermolecular charge transfer (PICT).
Abstract: A generation 1 poly(propylene thiophenoimine)-co-poly(ethylenedioxy thiophene) (G1PPT-co-PEDOT) star copolymer, which exhibits a strong optical absorption over a broad range in the ultraviolet–visible (UV-Vis) region and with good electro/conductive properties, was chemically prepared for the first time. Synthesis of the star copolymer, G1PPT-co-PEDOT was confirmed by spectroscopic studies. Indeed, the disappearance of the very high intensity bands, C–H bending at α-position (687 cm−1), and C=N stretching (1620 cm−1) in the Fourier transform infrared spectroscopy (FTIR) of G1PPT-co-PEDOT, which were initially present in the spectrum of the thiolated starting material, G1PPT, confirmed copolymerization. Furthermore, a large bathochromic shift in the onset wavelength of the UV-Vis absorbance spectra from 367 nm in G1PPT to 674 nm in G1PPT-co-PEDOT further attests of successful copolymerization. The electrochemical analysis of G1PPT-co-PEDOT achieved a highest occupied molecular orbital (HOMO) energy level value of 5.3 eV, which is reminiscent of the value for an ideal electron-donor material. Photoluminescence quenching of up to 82% was observed in solution blends of the G1PPT-co-PEDOT star copolymer and N,N′-diisopropyl naphthalene diimide (NDI). This demonstrates the occurrence of photoinduced intermolecular charge transfer (PICT) from the electron-donating G1PPT-co-PEDOT to the electron accepting NDI, a good property, beneficial for optoelectronic and photovoltaic applications.

5 citations

Journal ArticleDOI
01 Dec 2022
TL;DR: In this article , the symmetric and asymmetric perylenediimide (PDI)-based organic ligands Ph-PDI-Ph (1), Pyr-PDIs-Pyr (2), and Pyr-PI-Ph(3) were synthesized using thermal evaporation and their photodiode performances were examined under the irradiation of 100 mW.
Abstract: • Synthesis of symmetric and asymmetric PDIs (X = C or N). • The fabricated of PDI-based Al/pSi/PDIs/Au as OPV. • An analytical overview on the photoelectronic performances. • Theoretical studies; DFT, TD-DFT, CPCM and MEP. The symmetric and asymmetric perylenediimide (PDI)-based organic ligands Ph-PDI-Ph (1), Pyr-PDI-Pyr (2), and Pyr-PDI-Ph (3) were synthesized. Au/(Pyr-PDI-Ph)/ p -Si ( D1 ), and Au/(Ph-PDI-Ph)/ p -Si ( D2 ) devices were fabricated using thermal evaporation and their photodiode performances were examined under the irradiation of 100 mW.cm −2 at −2 V. In addition to the analysis of photodiode performances, the electrical properties depending on temperature and frequency of these structures were calculated using three different methods, which are the thermionic emission, Norde function, and Cheung&Cheung function. Furthermore, the molecular geometry, electronic absorption spectra, HOMO-LUMO and MEP surface analysis of the molecules mentioned were computed using the DFT/B3LYP method with 6-31 G (d,p) basis set and DFT calculations supported both the non-planar structures or propeller structures and compatibility of the theoretical results with the experimental data. The results supported that the fabricated D1 and D2 devices can form a basis for practical applications in optoelectronic device applications, especially photodiodes and photodetectors.

4 citations

Journal ArticleDOI
TL;DR: In this article , a series of thermoplastic olefins (TPOs) with NIR reflective pigment (this article), NIR transparent pigment (TRANS) and mixture of these two pigments in specific loading levels were compared to the TPO compounds containing conventional pigments.
Abstract: Absorption of the near-infrared (NIR) region of solar irradiance spectrum of the sunlight causes increase of the temperature of black inner parts of vehicles. The surface temperature of these parts can be decreased by reflecting or transmitting the NIR region of sunlight. This study intends to decrease the temperature of black surfaces that are exposed to sunlight and create cool black surfaces by preventing the absorption of the NIR region of the solar irradiance spectrum. Incorporation of cool black pigments having NIR reflective or NIR transparent properties into thermoplastic olefins (TPOs) was studied. A series of compounds were generated containing only NIR reflective pigment (REF), only NIR transparent pigment (TRANS) and the mixture of these two pigments in specific loading levels. The surface temperature of black TPO compounds were compared to the TPO compounds containing conventional pigments. Results showed that an optimum TPO compound having cool black surface was obtained with the sample MIX-5 (2% REF + 0.4% TRANS) which demonstrated 28.2% cooling compared to samples with carbon black, 9.04 MPa tensile strength, 1200% elongation at break and mold shrinkage values of 0.61% and 0.11% at directions parallel and perpendicular to flow respectively.
References
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Journal ArticleDOI
TL;DR: In this paper, a two-layer organic photovoltaic cell was fabricated from copper phthalocyanine and a perylene tetracarboxylic derivative, achieving a power conversion efficiency of about 1% under simulated AM2 illumination.
Abstract: A thin‐film, two‐layer organic photovoltaiccell has been fabricated from copper phthalocyanine and a perylene tetracarboxylic derivative. A power conversion efficiency of about 1% has been achieved under simulated AM2 illumination. A novel feature of the device is that the charge‐generation efficiency is relatively independent of the bias voltage, resulting in cells with fill factor values as high as 0.65. The interface between the two organic materials, rather than the electrode/organic contacts, is crucial in determining the photovoltaicproperties of the cell.

4,717 citations

Journal ArticleDOI
TL;DR: This review summarizes the developments in small molecular donors, acceptors, and donor-acceptor dyad systems for high-performance multilayer, bulk heterojunction, and single-component OPVs and focuses on correlations of molecular chemical structures with properties, such as absorption, energy levels, charge mobilities, and photovoltaic performances.
Abstract: Organic photovoltaic cells (OPVs) are a promising cost-effective alternative to silicon-based solar cells, and possess light-weight, low-cost, and flexibility advantages. Significant progress has been achieved in the development of novel photovoltaic materials and device structures in the last decade. Nowadays small molecular semiconductors for OPVs have attracted considerable attention, due to their advantages over their polymer counterparts, including well-defined molecular structure, definite molecular weight, and high purity without batch to batch variations. The highest power conversion efficiencies of OPVs based on small molecular donor/fullerene acceptors or polymeric donor/fullerene acceptors are up to 6.7% and 8.3%, respectively, and meanwhile nonfullerene acceptors have also exhibited some promising results. In this review we summarize the developments in small molecular donors, acceptors (fullerene derivatives and nonfullerene molecules), and donor–acceptor dyad systems for high-performance multilayer, bulk heterojunction, and single-component OPVs. We focus on correlations of molecular chemical structures with properties, such as absorption, energy levels, charge mobilities, and photovoltaic performances. This structure–property relationship analysis may guide rational structural design and evaluation of photovoltaic materials (253 references).

1,515 citations

Journal ArticleDOI
TL;DR: An electron-transport polymer with good solution processibility, excellent thermal stability, and high electron affinity based on alternating perylene diimide and dithienothiophene units has been synthesized.
Abstract: An electron-transport polymer with good solution processibility, excellent thermal stability, and high electron affinity based on alternating perylene diimide and dithienothiophene units has been synthesized Electron mobilities as high as 13 × 10-2 cm2 V-1 s-1 have been measured in field-effect transistor geometry The polymer shows broad absorptions throughout the visible and extending into the near-IR A power conversion efficiency of over 1%, under simulated AM 15, 100 mW/cm2, was measured for a single-layer solar cell using this polymer as an acceptor and a polythiophene derivative as a donor

1,091 citations

Journal ArticleDOI
TL;DR: The basic working principles and the state of the art device design of bulk heterojunction solar cells are reviewed and the importance of high power conversion efficiencies for the commercial exploitation is outlined and different efficiency models for bulk heterovoltaic cells are discussed.

923 citations

Journal ArticleDOI
TL;DR: In this paper, four soluble perylene diimide derivatives (PDIs) have been prepared and their UV-visible and photoluminescence (PL) spectroscopy, cyclic voltammetry (CV) and thermal properties were studied.
Abstract: Four soluble perylene diimide derivatives (PDIs) have been prepared and their UV–visible and photoluminescence (PL) spectroscopy, cyclic voltammetry (CV) and thermal properties were studied. ITO/PEDOT∶PSS/poly(3-hexylthiophene) (P3HT)∶PDIs/LiF/Al photovoltaic devices were fabricated with PDIs as electron accepting and transporting materials. The highest incident photon-to-current conversion efficiency (IPCE) of 19% at 495 nm and the power conversion efficiency (PCE) of 0.18% under AM 1.5 (100 mW cm−2) with a short-circuit current density (JSC) of 1.32 mA cm−2, an open circuit voltage (VOC) of 0.36 V, and a fill factor (FF) of 0.38 have been achieved with 1 ∶ 4 ratio of P3HT ∶ N,N′-di(1-nonadecyl)perylene-3,4,9,10-bis(dicarboximide) (PDI-C9) after annealing at 80 °C for 1 h. 1,7-Bis(N-pyrrolidinyl)-N,N′-dicyclohexyl-3,4,9,10-perylenebis(dicarboximide) (5-PDI), which has the electron donating pyrrolidinyl group, absorbed the long wavelength region to give IPCE onset higher than 750 nm and the pyrrolidinyl group also raised the LUMO level of 5-PDI to render the high VOC (up to 0.71 V) in photovoltaic device.

278 citations

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