Small Donor–Acceptor Molecules Based on a Quinoline–Fluorene System with Promising Photovoltaic Properties

Słodek, Aneta; Matussek, Marek; Filapek, Michał; Szafraniec‐Gorol, Grażyna; Szłapa, Agata; Grudzka-Flak, Iwona; Szczurek, Magdalena; Małecki, Jan Grzegorz; Maroń, Anna; Schab‐Balcerzak, Ewa; Nowak, E.; Sanetra, J.; Olejnik, Marian; Danikiewicz, Witold; Krompiec, Stanisław

doi:10.1002/ejoc.201600318

Cited by 28 publications

(14 citation statements)

References 49 publications

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“…Subsequently, prior deprotection of II using tetrabutylammonium fluoride (TBAF) followed by in-situ [Pd]catalyzed reaction with 2-bromodibenzothiophene gave compound 1a a 40% yield. The compounds 1b and 1c were obtained by Sonogashira cross-coupling of I with previously synthesized 4-[(trimethylsilyl)ethynyl]arenes (Scheme 2) [33,34]. Finally, the broadly used Knoevenagel condensation of 1a-1c with cyanoacetic acid (Scheme 3) gave the desired compounds 2a-2c average yields of 45-55%.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Investigations of New Phenothiazine-Based Compounds for Dye-Sensitized Solar Cells with Theoretical Insight

Słodek

Zych²,

Szafraniec‐Gorol

et al. 2020

Materials

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New D-π-D-π-A low-molecular-weight compounds, based on a phenothiazine scaffold linked via an acetylene unit with various donor moiety and cyanoacrylic acid anchoring groups, respectively, were successfully synthesized. The prepared phenothiazine dyes were entirely characterized using nuclear magnetic resonance (NMR) spectroscopy and elemental analysis. The compounds were designed to study the relationship between end-capping donor groups’ structure on their optoelectronic and thermal properties as well as the dye-sensitized solar cells’ performance. The effect of π-conjugation enlargement by incorporation of different heterocyclic substituents possessing various electron–donor affinities was systematically experimentally and theoretically examined. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations were implemented to determine the electronic properties of the novel molecules.

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Section: Synthesis and Characterizationmentioning

confidence: 99%

Investigations of New Phenothiazine-Based Compounds for Dye-Sensitized Solar Cells with Theoretical Insight

Słodek

Zych²,

Szafraniec‐Gorol

et al. 2020

Materials

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“…In the later work 92 the same group described the series of quinolines 103b, bearing fluorenyl fragment at the position 2. These compounds exhibit emission with λ em in the range of 400−560 nm, the presence of nitro group leads to the red shift; the luminescence quantum yield from 0.6 to 0.30.…”

Section: Structures 100-103mentioning

confidence: 99%

Functionalized benzazines as luminescent materials and components for optoelectronics

Носова¹,

Achelle²,

Lipunova³

et al. 2019

Russ. Chem. Rev.

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Extensive research on the synthesis and application of benzazine derivatives for electronic devices, luminescent elements, photoelectric conversion elements, and image sensors has been published recently. In the frames of this review article data obtained within the period 2012−2018 on the synthesis and optical properties of functionalized quinolines, quinoxalines and quinazolines are considered. Arylvinyl-, arylethynyl-and (het)arylderivatives of these benzazines, their photoluminescence and photoisomerisation are discussed. Examples of photosensitive annelated, oligo-and polymeric benzazines and also coordination compounds with benzazine ligands are reviewed.

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“…Device with ZnP‐C60 did not show any light effect while the device made H2P‐C60 dyad (nonencapsulated and unoptimized) showed promising photovoltaic property. From OPV device J‐V characteristics, we calculated the open circuit voltage (V oc ) approximately 0.49 V, short circuit current (J sc ) of approximately 50 μA/cm 2 , and high‐fill factor of 0.57 that are much higher than the recently reported device for quinoline‐fluorene‐based system and previous reports (see ESI) . Thus, the device data prove the concept of nonmetallated porphyrin‐fullerene dyad to be a better candidate in organic solar cell compared with metallated dyads.…”

Section: Excited State Interaction Studymentioning

confidence: 99%

Comparative charge transfer studies in nonmetallated and metallated porphyrin fullerene dyads

Gupta

Naqvi

Jewariya

et al. 2017

J of Physical Organic Chem

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Single material organic solar cells become an interesting area of research to overcome the challenges with efficient charge separation efficiencies in conventional organic solar cells. In this article, we have synthesized nonmetallated and metallated porphyrin-fullerene dyad materials (H2P-C60 and ZnP-C60, respectively) with simple structure, comprehensively studied their charge transfer mechanism, and established a proof of concept that nonmetallated porphyrin-fullerene dyads are better candidates to be used in organic solar cells compared with metallated dyads. Absorption and electrochemical analysis revealed the ground state electronic interactions between donor-acceptor moieties in both types of dyads. Driving force (−ΔG o ET ) for intramolecular electron transfer process was calculated by first oxidation and reduction potentials of dyads. The excited state electronic interactions were characterized by time-resolved fluorescence and pump-probe transient absorption experiments. Strong fluorescence quenching of porphyrin along with reduced lifetimes in dyads due to deactivation of singlet excited states by photoinduced charge transfer process between porphyrin/Zn-porphyrin core and fullerene in different polarity solvents was observed. Transient absorption spectroscopy was also applied to identify the transient spectral features, ie, cationic (H2P + /ZnP + ) and anionic (C 60 − ) radicals formed because of the charge separation in both types of dyads. Finally, organic solar cell device was also fabricated using the dyads. We obtained higher V oc , J sc , and fill factor in single material organic solar cell using H2P-C60 compared to previous reports.

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Small Donor–Acceptor Molecules Based on a Quinoline–Fluorene System with Promising Photovoltaic Properties

Cited by 28 publications

References 49 publications

Investigations of New Phenothiazine-Based Compounds for Dye-Sensitized Solar Cells with Theoretical Insight

Investigations of New Phenothiazine-Based Compounds for Dye-Sensitized Solar Cells with Theoretical Insight

Functionalized benzazines as luminescent materials and components for optoelectronics

Comparative charge transfer studies in nonmetallated and metallated porphyrin fullerene dyads

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