Sergey Dayneko - Academia.edu (original) (raw)

Papers by Sergey Dayneko

Research paper thumbnail of Improved performance of solution processed OLEDs using N-annulated perylene diimide emitters with bulky side-chains

Materials Advances, 2021

We report the design and synthesis of three N-annulated perylene diimide (PDI) compounds containi... more We report the design and synthesis of three N-annulated perylene diimide (PDI) compounds containing sterically bulky alkyl-substituted benzyl moieties (PDI-X, where X = 1, 2, 3) and explore their use as light emitting materials in solution processed OLED devices.

Research paper thumbnail of Tailored ZnO Functional Nanomaterials for Solution‐Processed Quantum‐Dot Light‐Emitting Diodes

Advanced Photonics Research

Research paper thumbnail of Synthesis, characterization and use of benzothioxanthene imide based dimers

Chemical Communications, 2020

The synthesis of benzothioxanthene imide based dimers and their first use in light emitting devic... more The synthesis of benzothioxanthene imide based dimers and their first use in light emitting devices are reported herein.

Research paper thumbnail of Solution processed red organic light-emitting-diodes using an N-annulated perylene diimide fluorophore

Journal of Materials Chemistry C, 2020

In this contribution we report on solution processed red OLEDs based upon an N-annulated perylene... more In this contribution we report on solution processed red OLEDs based upon an N-annulated perylene diimide dimer, namely tPDI2N-EH, a red-light emitting molecule.

Research paper thumbnail of Red Organic Light-Emitting-Diodes based on a N-Annulated Perylene Diimide Dimer

In this contribution we report on solution processed red OLEDs based upon a N-annulated perylene ... more In this contribution we report on solution processed red OLEDs based upon a N-annulated perylene diimide dimer, namely tPDI2N-EH, a red-light emitting molecule. OLED devices with the architecture of glass/ITO/PEDOT:PSS/EML/LiF/Ag (EML = emitting layer) were fabricated with EMLs comprised of tPDI2N-EH neat and blended with poly (9,9-dicotylfluorene, PFO), all solution processed from non-halogenated solvents. The photophysical and electrophysical performance of PFO:tPDI2N-EH-blend films with different composition ratios were investigated. The PFO:tPDI2N-EH-based OLEDs with a 2:18 ratio exhibited best performance. The PFO:tPDI2N-EH-based OLEDs gave red electroluminescence with the emission wavelength of 635 nm and the CIE (international commission on illumination) coordinates of (x = 0.672, y = 0.321). OLEDs with EMLs fabricated using roll-to-roll compatible methods are also demonstrated.

Research paper thumbnail of Interfacial ZnO Modification Using a Carboxylic Acid Functionalized N-Annulated Perylene Diimide for Inverted Type Organic Photovoltaics

ACS Applied Electronic Materials, 2019

This study reports the modification of the zinc oxide cathodic electrode with an Nannulated peryl... more This study reports the modification of the zinc oxide cathodic electrode with an Nannulated perylene diimide molecule functionalized with a carboxylic acid, namely (HOOC 5triazole) PDIN-hex, for the improvement of inverted-type organic photovoltaics. The new interlayer "IL-1" was synthesized using "click" chemistry and incorporated into the photovoltaic device structure using solution processing methods. The organic modified zinc oxide layer was characterized using optical absorption spectroscopy, contact angle measurements, and Kelvin probe force microscopy. IL-1 was retained on the zinc oxide surface and lowered the electrode work function from 4.5 eV to 4.1 eV, the low work function is crucial for any cathodic interlayer to match with the LUMO energy levels of acceptor materials for better charge extraction and electron collection properties. Bulk heterojunction organic photovoltaic devices utilizing this interlayer (compared to only zinc oxide) exhibited increases in power conversion efficiency from 20-33% for those with active layer blends based on both fullerene and non-fullerene acceptors.

Research paper thumbnail of Ternary organic solar cells: using molecular donor or acceptor third components to increase open circuit voltage

New Journal of Chemistry, 2019

The addition of donor or acceptor type molecular semiconductors to PBDB-T:PC60BM based organic ph... more The addition of donor or acceptor type molecular semiconductors to PBDB-T:PC60BM based organic photovoltaics leads to increases in open circuit-voltages and overall power conversion efficiencies.

Research paper thumbnail of Bromination of the benzothioxanthene Bloc: toward new π-conjugated systems for organic electronic applications

Journal of Materials Chemistry C, 2018

The synthesis for monobrominated benzothioxanthene is reported, which is then employed in common ... more The synthesis for monobrominated benzothioxanthene is reported, which is then employed in common palladium catalyzed coupling reactions for novel organic semiconductors.

Research paper thumbnail of Synthesis of a Perylene Diimide Dimer with Pyrrolic N-H Bonds and N-Functionalized Derivatives for Organic Field-Effect Transistors and Organic Solar Cells

European Journal of Organic Chemistry, 2018

This study reports on the new and optimized synthesis of an N-annulated perylene diimide dimer wi... more This study reports on the new and optimized synthesis of an N-annulated perylene diimide dimer with functional N-H moieties. The presence of two N-H moieties renders the dimer relatively insoluble in most organic solvents. The dimer is easily functionalized with electron donating hexyl chains or electron withdrawing tert-butyloxycarbonyl (tBOC) groups to yield highly soluble materials. The tBOC groups can be thermally cleaved in the thin-film to give the

Research paper thumbnail of A triazatruxene-based molecular dyad for single-component organic solar cells

Chemistry Squared, 2018

The synthesis, characterization and use of a new donor-acceptor molecular dyad in single componen... more The synthesis, characterization and use of a new donor-acceptor molecular dyad in single component organic solar cells are reported. The dyad, composed of a triazatruxene-based push-pull 'donor' unit linked to a C60 'acceptor' unit through a non-conjugated σ connector, led to promising power conversion efficiencies of 0.6% when embedded in simple devices exhibiting the architecture: indium tin oxide (ITO)/poly(3,4-ethylenedioxythiophene): polystyrene sulfonic acid (PEDOT:PSS)/dyad/Al.

Research paper thumbnail of Direct (Hetero)Arylation Polymerization of a Spirobifluorene and a Dithienyl-Diketopyrrolopyrrole Derivative: New Donor Polymers for Organic Solar Cells

Molecules (Basel, Switzerland), Jan 20, 2018

The synthesis and preliminary evaluation as donor material for organic photovoltaics of the poly(... more The synthesis and preliminary evaluation as donor material for organic photovoltaics of the poly(diketopyrrolopyrrole-spirobifluorene) () is reported herein. Prepared via homogeneous and heterogeneous direct (hetero)arylation polymerization (DHAP), through the use of different catalytic systems, conjugated polymers with comparable molecular weights were obtained. The polymers exhibited strong optical absorption out to 700 nm as thin-films and had appropriate electronic energy levels for use as a donor with . Bulk heterojunction solar cells were fabricated giving power conversion efficiencies above 4%. These results reveal the potential of such polymers prepared in only three steps from affordable and commercially available starting materials.

Research paper thumbnail of Applying direct heteroarylation synthesis to evaluate organic dyes as the core component in PDI-based molecular materials for fullerene-free organic solar cells

Journal of Materials Chemistry A, 2017

A streamlined synthetic approach to easily access complex pi-conjugated molecular materials.

Research paper thumbnail of N-Annulated perylene diimide dimers: acetylene linkers as a strategy for controlling structural conformation and the impact on physical, electronic, optical and photovoltaic properties

Journal of Materials Chemistry C, 2017

The geometry of organic π-conjugated small molecules can impact the morphology of blended-thin fi... more The geometry of organic π-conjugated small molecules can impact the morphology of blended-thin films and subsequent performance in opto-electronic devices.

Research paper thumbnail of N-annulated perylene diimide dimers: the effect of thiophene bridges on physical, electronic, optical, and photovoltaic properties

Sustainable Energy & Fuels, 2017

In this work, we report on the synthesis, characterization, and photovoltaic properties of two ne... more In this work, we report on the synthesis, characterization, and photovoltaic properties of two new N-annulated PDI derivatives connected with one (M1) or two (M2) thiophene bridging units and directly compare to a twisted PDI dimer with no thiophene units (tPDI-Hex).

Research paper thumbnail of A non-fullerene acceptor with a diagnostic morphological handle for streamlined screening of donor materials in organic solar cells

Journal of Materials Chemistry A, 2017

Utilizing the N-annulated PDI acceptor PDI–DPP–PDI, a simple air-processed and air-tested organic... more Utilizing the N-annulated PDI acceptor PDI–DPP–PDI, a simple air-processed and air-tested organic photovoltaic device fabrication procedure has been established to streamline the screening of donor materials.

Research paper thumbnail of Correction: An unsymmetrical non-fullerene acceptor: synthesis via direct heteroarylation, self-assembly, and utility as a low energy absorber in organic photovoltaic cells

Chem. Commun., 2017

Correction for ‘An unsymmetrical non-fullerene acceptor: synthesis via direct heteroarylation, se... more Correction for ‘An unsymmetrical non-fullerene acceptor: synthesis via direct heteroarylation, self-assembly, and utility as a low energy absorber in organic photovoltaic cells’ by Abby-Jo Payne et al., Chem. Commun., 2017, 53, 10168–10171.

Research paper thumbnail of Simply Complex: The Efficient Synthesis of an Intricate Molecular Acceptor for High-Performance Air-Processed and Air-Tested Fullerene-Free Organic Solar Cells

Chemistry of Materials, 2017

Research paper thumbnail of An unsymmetrical non-fullerene acceptor: synthesis via direct heteroarylation, self-assembly, and utility as a low energy absorber in organic photovoltaic cells

Chemical communications (Cambridge, England), Jan 30, 2017

This study reports on the design and synthesis of an unsymmetrical π-conjugated organic molecule ... more This study reports on the design and synthesis of an unsymmetrical π-conjugated organic molecule composed of perylene diimide, thienyl diketopyrrolopyrrole, and indoloquinoxaline pieced together using direct heteroarylation. This material demonstrates unprecedented response in the thin-film upon post-deposition solvent vapor annealing, resulting in dramatic red-shifts in optical absorption. Such changes were utilized to enhance photocurrent generation in P3HT based organic solar cells.

Research paper thumbnail of Fullerene-free polymer solar cells processed from non-halogenated solvents in air with PCE of 4.8%

Chemical Communications, 2017

Progress towards practical organic solar cells amenable to large scale production is reported.

Research paper thumbnail of Light‐Emitting Diodes: Highly Efficient Quantum Dot Light‐Emitting Diodes by Inserting Multiple Poly(methyl methacrylate) as Electron‐Blocking Layers (Adv. Funct. Mater. 50/2019)

Advanced Functional Materials, 2019

In article number 1906742, Majid Pahlevani, Yujun Shi, and co-workers present a new quantum-dot l... more In article number 1906742, Majid Pahlevani, Yujun Shi, and co-workers present a new quantum-dot light-emitting diode device architecture, integrating multiple poly(methylmethacrylate) (PMMA) electron blocking layers between a pair of red-emitting QD layers. The experimental optimization and numerical simulation demonstrate significant improvement in brightness and current efficiency from the structure consisting of two PMMA and three QD layers due to the reduction in electron leakage by the addition of PMMA layers.

Research paper thumbnail of Improved performance of solution processed OLEDs using N-annulated perylene diimide emitters with bulky side-chains

Materials Advances, 2021

We report the design and synthesis of three N-annulated perylene diimide (PDI) compounds containi... more We report the design and synthesis of three N-annulated perylene diimide (PDI) compounds containing sterically bulky alkyl-substituted benzyl moieties (PDI-X, where X = 1, 2, 3) and explore their use as light emitting materials in solution processed OLED devices.

Research paper thumbnail of Tailored ZnO Functional Nanomaterials for Solution‐Processed Quantum‐Dot Light‐Emitting Diodes

Advanced Photonics Research

Research paper thumbnail of Synthesis, characterization and use of benzothioxanthene imide based dimers

Chemical Communications, 2020

The synthesis of benzothioxanthene imide based dimers and their first use in light emitting devic... more The synthesis of benzothioxanthene imide based dimers and their first use in light emitting devices are reported herein.

Research paper thumbnail of Solution processed red organic light-emitting-diodes using an N-annulated perylene diimide fluorophore

Journal of Materials Chemistry C, 2020

In this contribution we report on solution processed red OLEDs based upon an N-annulated perylene... more In this contribution we report on solution processed red OLEDs based upon an N-annulated perylene diimide dimer, namely tPDI2N-EH, a red-light emitting molecule.

Research paper thumbnail of Red Organic Light-Emitting-Diodes based on a N-Annulated Perylene Diimide Dimer

In this contribution we report on solution processed red OLEDs based upon a N-annulated perylene ... more In this contribution we report on solution processed red OLEDs based upon a N-annulated perylene diimide dimer, namely tPDI2N-EH, a red-light emitting molecule. OLED devices with the architecture of glass/ITO/PEDOT:PSS/EML/LiF/Ag (EML = emitting layer) were fabricated with EMLs comprised of tPDI2N-EH neat and blended with poly (9,9-dicotylfluorene, PFO), all solution processed from non-halogenated solvents. The photophysical and electrophysical performance of PFO:tPDI2N-EH-blend films with different composition ratios were investigated. The PFO:tPDI2N-EH-based OLEDs with a 2:18 ratio exhibited best performance. The PFO:tPDI2N-EH-based OLEDs gave red electroluminescence with the emission wavelength of 635 nm and the CIE (international commission on illumination) coordinates of (x = 0.672, y = 0.321). OLEDs with EMLs fabricated using roll-to-roll compatible methods are also demonstrated.

Research paper thumbnail of Interfacial ZnO Modification Using a Carboxylic Acid Functionalized N-Annulated Perylene Diimide for Inverted Type Organic Photovoltaics

ACS Applied Electronic Materials, 2019

This study reports the modification of the zinc oxide cathodic electrode with an Nannulated peryl... more This study reports the modification of the zinc oxide cathodic electrode with an Nannulated perylene diimide molecule functionalized with a carboxylic acid, namely (HOOC 5triazole) PDIN-hex, for the improvement of inverted-type organic photovoltaics. The new interlayer "IL-1" was synthesized using "click" chemistry and incorporated into the photovoltaic device structure using solution processing methods. The organic modified zinc oxide layer was characterized using optical absorption spectroscopy, contact angle measurements, and Kelvin probe force microscopy. IL-1 was retained on the zinc oxide surface and lowered the electrode work function from 4.5 eV to 4.1 eV, the low work function is crucial for any cathodic interlayer to match with the LUMO energy levels of acceptor materials for better charge extraction and electron collection properties. Bulk heterojunction organic photovoltaic devices utilizing this interlayer (compared to only zinc oxide) exhibited increases in power conversion efficiency from 20-33% for those with active layer blends based on both fullerene and non-fullerene acceptors.

Research paper thumbnail of Ternary organic solar cells: using molecular donor or acceptor third components to increase open circuit voltage

New Journal of Chemistry, 2019

The addition of donor or acceptor type molecular semiconductors to PBDB-T:PC60BM based organic ph... more The addition of donor or acceptor type molecular semiconductors to PBDB-T:PC60BM based organic photovoltaics leads to increases in open circuit-voltages and overall power conversion efficiencies.

Research paper thumbnail of Bromination of the benzothioxanthene Bloc: toward new π-conjugated systems for organic electronic applications

Journal of Materials Chemistry C, 2018

The synthesis for monobrominated benzothioxanthene is reported, which is then employed in common ... more The synthesis for monobrominated benzothioxanthene is reported, which is then employed in common palladium catalyzed coupling reactions for novel organic semiconductors.

Research paper thumbnail of Synthesis of a Perylene Diimide Dimer with Pyrrolic N-H Bonds and N-Functionalized Derivatives for Organic Field-Effect Transistors and Organic Solar Cells

European Journal of Organic Chemistry, 2018

This study reports on the new and optimized synthesis of an N-annulated perylene diimide dimer wi... more This study reports on the new and optimized synthesis of an N-annulated perylene diimide dimer with functional N-H moieties. The presence of two N-H moieties renders the dimer relatively insoluble in most organic solvents. The dimer is easily functionalized with electron donating hexyl chains or electron withdrawing tert-butyloxycarbonyl (tBOC) groups to yield highly soluble materials. The tBOC groups can be thermally cleaved in the thin-film to give the

Research paper thumbnail of A triazatruxene-based molecular dyad for single-component organic solar cells

Chemistry Squared, 2018

The synthesis, characterization and use of a new donor-acceptor molecular dyad in single componen... more The synthesis, characterization and use of a new donor-acceptor molecular dyad in single component organic solar cells are reported. The dyad, composed of a triazatruxene-based push-pull 'donor' unit linked to a C60 'acceptor' unit through a non-conjugated σ connector, led to promising power conversion efficiencies of 0.6% when embedded in simple devices exhibiting the architecture: indium tin oxide (ITO)/poly(3,4-ethylenedioxythiophene): polystyrene sulfonic acid (PEDOT:PSS)/dyad/Al.

Research paper thumbnail of Direct (Hetero)Arylation Polymerization of a Spirobifluorene and a Dithienyl-Diketopyrrolopyrrole Derivative: New Donor Polymers for Organic Solar Cells

Molecules (Basel, Switzerland), Jan 20, 2018

The synthesis and preliminary evaluation as donor material for organic photovoltaics of the poly(... more The synthesis and preliminary evaluation as donor material for organic photovoltaics of the poly(diketopyrrolopyrrole-spirobifluorene) () is reported herein. Prepared via homogeneous and heterogeneous direct (hetero)arylation polymerization (DHAP), through the use of different catalytic systems, conjugated polymers with comparable molecular weights were obtained. The polymers exhibited strong optical absorption out to 700 nm as thin-films and had appropriate electronic energy levels for use as a donor with . Bulk heterojunction solar cells were fabricated giving power conversion efficiencies above 4%. These results reveal the potential of such polymers prepared in only three steps from affordable and commercially available starting materials.

Research paper thumbnail of Applying direct heteroarylation synthesis to evaluate organic dyes as the core component in PDI-based molecular materials for fullerene-free organic solar cells

Journal of Materials Chemistry A, 2017

A streamlined synthetic approach to easily access complex pi-conjugated molecular materials.

Research paper thumbnail of N-Annulated perylene diimide dimers: acetylene linkers as a strategy for controlling structural conformation and the impact on physical, electronic, optical and photovoltaic properties

Journal of Materials Chemistry C, 2017

The geometry of organic π-conjugated small molecules can impact the morphology of blended-thin fi... more The geometry of organic π-conjugated small molecules can impact the morphology of blended-thin films and subsequent performance in opto-electronic devices.

Research paper thumbnail of N-annulated perylene diimide dimers: the effect of thiophene bridges on physical, electronic, optical, and photovoltaic properties

Sustainable Energy & Fuels, 2017

In this work, we report on the synthesis, characterization, and photovoltaic properties of two ne... more In this work, we report on the synthesis, characterization, and photovoltaic properties of two new N-annulated PDI derivatives connected with one (M1) or two (M2) thiophene bridging units and directly compare to a twisted PDI dimer with no thiophene units (tPDI-Hex).

Research paper thumbnail of A non-fullerene acceptor with a diagnostic morphological handle for streamlined screening of donor materials in organic solar cells

Journal of Materials Chemistry A, 2017

Utilizing the N-annulated PDI acceptor PDI–DPP–PDI, a simple air-processed and air-tested organic... more Utilizing the N-annulated PDI acceptor PDI–DPP–PDI, a simple air-processed and air-tested organic photovoltaic device fabrication procedure has been established to streamline the screening of donor materials.

Research paper thumbnail of Correction: An unsymmetrical non-fullerene acceptor: synthesis via direct heteroarylation, self-assembly, and utility as a low energy absorber in organic photovoltaic cells

Chem. Commun., 2017

Correction for ‘An unsymmetrical non-fullerene acceptor: synthesis via direct heteroarylation, se... more Correction for ‘An unsymmetrical non-fullerene acceptor: synthesis via direct heteroarylation, self-assembly, and utility as a low energy absorber in organic photovoltaic cells’ by Abby-Jo Payne et al., Chem. Commun., 2017, 53, 10168–10171.

Research paper thumbnail of Simply Complex: The Efficient Synthesis of an Intricate Molecular Acceptor for High-Performance Air-Processed and Air-Tested Fullerene-Free Organic Solar Cells

Chemistry of Materials, 2017

Research paper thumbnail of An unsymmetrical non-fullerene acceptor: synthesis via direct heteroarylation, self-assembly, and utility as a low energy absorber in organic photovoltaic cells

Chemical communications (Cambridge, England), Jan 30, 2017

This study reports on the design and synthesis of an unsymmetrical π-conjugated organic molecule ... more This study reports on the design and synthesis of an unsymmetrical π-conjugated organic molecule composed of perylene diimide, thienyl diketopyrrolopyrrole, and indoloquinoxaline pieced together using direct heteroarylation. This material demonstrates unprecedented response in the thin-film upon post-deposition solvent vapor annealing, resulting in dramatic red-shifts in optical absorption. Such changes were utilized to enhance photocurrent generation in P3HT based organic solar cells.

Research paper thumbnail of Fullerene-free polymer solar cells processed from non-halogenated solvents in air with PCE of 4.8%

Chemical Communications, 2017

Progress towards practical organic solar cells amenable to large scale production is reported.

Research paper thumbnail of Light‐Emitting Diodes: Highly Efficient Quantum Dot Light‐Emitting Diodes by Inserting Multiple Poly(methyl methacrylate) as Electron‐Blocking Layers (Adv. Funct. Mater. 50/2019)

Advanced Functional Materials, 2019

In article number 1906742, Majid Pahlevani, Yujun Shi, and co-workers present a new quantum-dot l... more In article number 1906742, Majid Pahlevani, Yujun Shi, and co-workers present a new quantum-dot light-emitting diode device architecture, integrating multiple poly(methylmethacrylate) (PMMA) electron blocking layers between a pair of red-emitting QD layers. The experimental optimization and numerical simulation demonstrate significant improvement in brightness and current efficiency from the structure consisting of two PMMA and three QD layers due to the reduction in electron leakage by the addition of PMMA layers.