Organic electron transport materials

• Joseph Cameron and
• Peter J. Skabara

Beilstein J. Org. Chem. 2024, 20, 672–674, doi:10.3762/bjoc.20.60

• transport materials for organic semiconductor devices due to their potential to be applied in various technologies. For example, such materials can be used to improve charge balance in the emissive layer of an organic light-emitting diode, charge extraction in perovskite solar cells or used as the

• , meaning organic materials can be used effectively in a range of applications. For example, while a non-fullerene acceptor material might not be suitable as an electron transport layer in OPVs due to dissolution of layers, it can used in perovskite solar cells where it can be successfully deposited through

• soluble in ethyl acetate, a green solvent, and solution-processed for PM6:Y6 bulk-heterojunction solar cells with power conversion efficiency > 13% [6]. In addition to orthogonal processing, it has been shown that treatment with base [7] or photo-crosslinking [8] can insolubilise solution-processed layers

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

• Eugeny Ivakhnenko,
• Vasily Malay,
• Pavel Knyazev,
• Nikita Merezhko,
• Nadezhda Makarova,
• Oleg Demidov,
• Gennady Borodkin,
• Andrey Starikov and
• Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

• probes, organic light-emitting diodes, and organic solar cells [2][7][8][9]. The principal way for the preparation of these heterocycles involves the coupling of 3H-phenoxazin-3-ones with variously functionalized aromatic amines. This is followed by the cyclization of the initially formed adducts [10][11

• potential for testing as potential donors for organic solar cells or as dye sensitizers for dye-sensitized solar cells [24][25]. Experimental All reagents and solvents were purchased from commercial sources (Aldrich) and used without additional purification. The compounds were characterized by 1H, 13C, and

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• ) [14][15][16][17][18][19]. These compounds are electron-rich, flat and electron-delocalized systems, properties that make them promising materials for the construction of conjugated energy-based semiconductors for OLEDs [20][21][22][23], perovskite solar cells [24][25], organic field-effect transistors

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• Abstract This review article provides a comprehensive overview of recent advancements in electron transport materials derived from quinoxaline, along with their applications in various electronic devices. We focus on their utilization in organic solar cells (OSCs), dye-sensitized solar cells (DSSCs

• processability compared to their inorganic counterparts [1][2]. Charge transport in organic semiconductors is a fundamental aspect that governs the performance and functionality of various organic semiconductor devices, such as organic solar cells (OSCs), organic field-effect transistors (OFETs), organic light

• conversion efficiencies (PCEs) of over 12% in polymer solar cells (PCS) when paired with the IDT acceptor [15], over 16% with the Y6 acceptor [16][17] and a champion PCE of 21.2% in perovskite solar cells [18]. This outstanding performance is attributed to the versatile and tunable nature of the Qx moiety

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• no barriers between the active layer and the CIL interface, indicating efficient charge extractions. In addition, to further confirm the charge extraction and recombination, the PAIOS (platform for all-in-one characterization of solar cells) tool from Fluxim was used to measure transient photocurrent

• functions of ITO, PEDOT:PSS, and Ag [30], as well as the energy levels of PM6, Y6, and the energy level range for the CILs used in this study. a) Current density-voltage (I–V) characterization under illumination, b) spectral response of the solar cells, c) I–V characteristics under dark, d) photocurrent vs

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• quinoxalinoporphyrins displayed a wide range of applications in many fields including molecular electronics [8][9][10]. Additionally, appropriately functionalized quinoxalinoporphyrin-based photosensitizers are of great interest in the area of dye-sensitized solar cells (DSSC) due to their strong absorption in the

Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors

• Grace A. Lowe

Beilstein J. Org. Chem. 2023, 19, 1198–1215, doi:10.3762/bjoc.19.88

• -sensitized solar cells [50][51]. As discussed, if a sacrificial donor is recycled in-situ it becomes a redox mediator. In artificial photosynthesis redox mediators are most commonly employed in Z-schemes. A Z-scheme describes the combination of two photocatalytic systems, one for photooxidation and one for

• are being developed in non-aqueous solvents. Amines, disulfide-forming thiolates, and NADH derivatives, such as benzimidazoles and acridines, are used as sacrificial donors. Other families of compounds used in other applications such as non-aqueous RFBs, dye-sensitized solar cells, and LOHCs will also

Strategies in the synthesis of dibenzo[b,f]heteropines

• David I. H. Maier,
• Barend C. B. Bezuidenhoudt and
• Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

• ; synthesis; Introduction The dibenzo[b,f]azepine (1a) scaffold (Figure 1) is featured in commercial pharmaceuticals [1] and other lead compounds [2][3][4], ligands [5][6] and in materials science with possible applications in organic light emitting diodes (OLEDs) [7] and dye-sensitized solar cells (DSSCs

• )-10,11-dihydro-5H-dibenzo[b,f]azepine-2,8-diyl)bis(N,N-diphenylaniline) (9) exhibits properties suitable for the use in organic light emitting diodes [7] whereas dyes 10–12 were found suitable for the use in dye-sensitised solar cells (Figure 4) [8][9][10]. Though analogous dibenzo[b,f]oxepines 1b, with

• dibenzo[b,f]heteropine template is an important feature in several commercial and lead active pharmaceutical ingredients, biologically active natural products, dyes in OLEDs and dye sensitive solar cells, and in certain ligands. This review provides an overview of the different synthetic strategies

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• medicinal chemistry. Owing to the strong absorption in the visible region, these 18π-electron systems also demonstrate excellent photoluminescence properties. Therefore, porphyrin hybrids have been widely used as efficient sensitizers for PDT applications and dye-sensitized solar cells (DSSCs). Because the

• 55 as sensitizers for dye-sensitized solar cells (DSSCs). These porphyrin conjugates were synthesized through the click reaction between azidoporphyrin 51 and alkynes 52 or 54. Further, porphyrin 57 bearing a CN and a COOH group was prepared by the treatment of porphyrin 55 with 2-cyanoacetic acid

• DSSCs. Moreover, porphyrin conjugates 107b- and 108b-based solar cells were fabricated, resulting in power conversion efficiencies (PCEs) of 3.82 and 5.16%, respectively. In addition, the authors discovered that dyads 108b containing shorter triazole bridges have a stronger absorption profile and higher

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

• Valentin H. K. Fell,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Eman J. Hussien and
• Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

• , which extends the degree of π-conjugation [1]. In this way, the HOMO–LUMO gap can be narrowed [2]. Low HOMO–LUMO gaps are desirable for organic solar cells as the maximum photoflux density of the sun is at ca. 700 nm, corresponding to 1.77 eV [3]. However, fused systems have the drawback of being prone

• (the basic unit of processors) [6], solar cells, and LEDs [7]. Inorganic compounds, e.g. III-V type inorganics are widely used, however, in recent years, organic molecules with semiconducting and fluorescent properties have emerged as an alternative with advantages such as solution processing [8][9][10

• example, ITIC (10), is shown in Figure 4. ITIC [17], in combination with polymer 11, achieved a power conversion efficiency (PCE) of 6.8%, which was the best value for NFA organic solar cells at the time of publication. Fluorination of ITIC, obtaining IT-4F (12), shown in Figure 5, reduced ELUMO. Combined

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

• Irina Fiodorova,
• Tomas Serevičius,
• Rokas Skaisgiris,
• Saulius Juršėnas and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

• , good electrical and optical properties, and easy chemical modification is a desired structural unit in organic structures targeted for numerous applications including organic photovoltaic solar cells (OPV) [12][13][14], organic field-effect transistors (OFETs) [15][16][17], chemical and biosensors [18

Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases

• Inaiá O. Rocha,
• Yuri G. Kappenberg,
• Wilian C. Rosa,
• Clarissa P. Frizzo,
• Nilo Zanatta,
• Marcos A. P. Martins,
• Isadora Tisoco,
• Bernardo A. Iglesias and
• Helio G. Bonacorso

Beilstein J. Org. Chem. 2021, 17, 2799–2811, doi:10.3762/bjoc.17.191

• interesting luminescent properties [14] that have attracted great interest because of their potential applicability in the composition of organic light-emitting diodes (OLED), organic solar cells (OSC), and biomolecular markers [15][16]. Moreover, the trifluoromethyl substituent (CF3) is an interesting

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

• Ilya A. P. Jourjine,
• Lukas Zeisel,
• Jürgen Krauß and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

• electronic and optical properties [16][17][18][19][20][21], utilized in LEDs, semiconducting polymers, and solar cells. Consequently, synthetic approaches to fluorenones have attracted large interest and numerous methodologically diverse approaches have been published in the past decades. Among these are

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• years because of their interesting photophysical, photochemical, and biological properties. They are currently the subject of research in several areas, which investigate their use in the biological field and their application in OLEDs, OFETs, polymeric materials, solar cells, and many other organic

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• acetylcholinesterase inhibitors [11][12][13], being LSPN223 the most potent compound (Figure 2). Furthermore, coumarin derivatives have been used as fluorescent probes, laser dyes, fluorescent chemosensors, light absorbers for solar cells, optical brighteners, and organic light emitting diodes (OLEDs) [14][15]. From a

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli,
• Noureddine Chaaben,
• Kamel Alimi,
• Stefan Jopp and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

• attention for their inspiring applications in the fields of solar cells [1][2][3], organic devices [4][5][6][7][8], and as chemosensors [9][10]. The acridine core (Figure 1), formed by two benzenes fused to a pyridine ring, is among the most extensively studied heterocyclic aromatic compounds. It has first

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• of functional materials are analyzed and summarized. These bisheterocycles can be used in the creation of organic solar cells, sensors, lithium ion batteries as well as in OFET and OLED technologies. The potentials of the use of polymer structures based on isoindigo as photoactive component in the

• photoelectrochemical reduction of water, as matrix for MALDI spectrometry and in photothermal cancer therapy are also shown. Data published over the past 5 years, including works published at the beginning of 2021, are given. Keywords: isoindigo; OFET; photoactive polymers; photovoltaics; solar cells; Introduction

• construction of polymeric materials for various purposes. Review Organic solar cells (OSCs) on the base of isoindigo derivatives Since the pioneering works on the use of isoindigo derivatives in the design of OSCs [3][4][5], specialists in this field have made significant progress in tuning and improving their

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2021, 17, 1374–1384, doi:10.3762/bjoc.17.96

• applications ranging from organic thin‐film transistors (OTFTs), organic light-emitting diodes (OLEDs), dye‐sensitized solar cells (DSSCs), fluorescent probes, organic photovoltaics (OPVs) to the high hole mobility semiconductors, blue light-emitting materials, nonlinear optical materials and so forth [5][6][7

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• solar cells [49][50]. In view of the globalization of energy problems, the issues of switching to alternative energy sources are becoming increasingly relevant. Solar energy, like the majority of renewable energy sources, is environmentally friendly and has almost no negative impact on the environment

• solar cells, [60]PCBM, as an example (Scheme 26). The mechanism of fullerene cyclopropanation is presented in Scheme 27. Using a similar procedure, the reaction of C60 and alkyl-4-benzoyl butyrate p-tosylhydrazone in the presence of sodium methoxide and pyridine, the following [6,6]-phenyl-C61-butyric

• in chloroform shows typical resonance signals of six hydrogen-bonded protons (Scheme 44) [162]. In order to improve the optical absorption of fullerene acceptors for utilization in solar cells with a bulk heterojunction, a series of dye–fullerene dyads with strong absorption in the visible region was

Synthesis and characterization of S,N-heterotetracenes

• Astrid Vogt,
• Florian Henne,
• Christoph Wetzel,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2020, 16, 2636–2644, doi:10.3762/bjoc.16.214

• properties, a variety of functionalized derivatives, mainly trimeric DTP (SN3) [18], pentameric SN5 [19][20][21][22][23], and hexameric SN6 [24][25][26][27][28], have been successfully implemented as active semiconducting components in organic solar cells [18][19][20][21][24][25][26], perovskite solar cells

• complementing the series, but did not yet describe synthetic details [7]. Xue et al. published a donor–acceptor photosensitizer for dye-sensitized solar cells, in which the N-phenylated SN4 unit serves as bridge between donor and acceptor moieties [34]. Further replacement of sulfur by nitrogen can lead to

• opposite effects. The basic SN4 and SN4'' frameworks represent novel core molecules for further functionalization, for example with terminal acceptor groups, leading to highly absorbing dye molecules for application in organic solar cells. Heteroacenes: tetrathienoacene (TTA), S,N-heteroacenes SN4, SN4

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• be irradiated at different wavelengths and inject electrons to the photocatalyst or vice versa. The same methodology is commonly applied in dye-sensitised solar cells [102]. Additionally, as only the surface of the support is functionalised with photoactive units, they are more likely to be

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

• Alessandra Del Tito,
• Havall Othman Abdulla,
• Davide Ravelli,
• Stefano Protti and
• Maurizio Fagnoni

Beilstein J. Org. Chem. 2020, 16, 1476–1488, doi:10.3762/bjoc.16.123

• the design of dye-sensitized solar cells (DSSC) [4]. Typical methods for the construction of a phenanthrene core involve transition-metal-catalyzed cycloisomerizations starting from arynes [5][6], o-alkynyl-biaryls [7][8], or substituted N-tosylhydrazones [9]. However, since the introduction in 1964

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

• Nuray Altinolcek,
• Ahmet Battal,
• Mustafa Tavasli,
• William J. Peveler,
• Holly A. Yu and
• Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

• synthesised solar cells (DSSCs) and sensors [1][2]. In OLEDs, carbazole derivatives are frequently used as host materials [3][4][5]. In this respect the most frequently used host materials are 1,3-bis(N-carbazolyl)benzene (mCP) [6] and polyvinylcarbazole (PVK) [7]. Carbazole derivatives, either just by

• multifunctionalisation [31]. In this work, we designed two novel 2-(N-hexylcarbazol-3’-yl)-4/5-formylpyridine compounds (7a and 7b), where 4/5-pyridinecarboxyaldehyde was attached to the 3-position of carbazole via the 2-position of the pyridine ring. These two compounds (7a and 7b) can be used in OLEDs, solar cells and

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

• Vuyisa Mzozoyana,
• Fanie R. van Heerden and
• Craig Grimmer

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

• coumarins have been identified from natural sources [1][2]. Coumarins have been reported to play a vital role as food and cosmetics constituents, cigarette additives, and dye-sensitized solar cells [3][4]. In addition, coumarins possess some biological activities such as anti-inflammatory [5], antitumor [6