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

Dyes in modern organic chemistry

• Heiko Ihmels

Beilstein J. Org. Chem. 2019, 15, 2798–2800, doi:10.3762/bjoc.15.272

• dyes also contribute as essential components in modern applications such as in OLEDs [5][6], solar cells [7][8], organic semiconductors [9], NLO materials [10], photopolymerization [11], or Chemistry 4.0 [12]. From its very beginning, dye chemistry is strongly connected to the scientific developments

Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction

• Nadezhda S. Demina,
• Nikita A. Kazin,
• Nikolay A. Rasputin,
• Roman A. Irgashev and
• Gennady L. Rusinov

Beilstein J. Org. Chem. 2019, 15, 2678–2683, doi:10.3762/bjoc.15.261

• light-harvesting dyes for dye-sensitized solar cells [1], electron-donating materials for bulk heterojunction solar cells [2][3][4], and p-type semiconductors for organic field-effect transistors [5][6][7]. Within the same context of organic semiconductor development, the bicyclic TT subunit has been

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• were computed by density functional theory modelling (DFT) and characterized through UV–vis spectroscopy and cyclic voltammetry (CV) measurements. Finally, we report preliminary results obtained using these functional dyes as photosensitizers in dye-sensitized solar cells (DSSCs). Keywords: boron

• -dipyrromethene; BODIPY; dye-sensitized solar cells; near-infrared absorbers; organic dyes; Introduction The past two decades have witnessed tremendous efforts to develop alternative photovoltaic (PV) technologies. Among them, dye-sensitized solar cells (DSSCs) display numerous advantages compared to its fully

• organic counterpart, i.e., bulk heterojunction solar cells, or other hybrid PV technologies such as perovskite solar cells. DSSCs can display satisfactory power conversion efficiencies (PCE) in the range of 10 to 14% [1][2][3] but also a long-term stability when specific electrolytes based on ionic

Synthesis, photophysical and electrochemical properties of pyridine, pyrazine and triazine-based (D–π–)₂A fluorescent dyes

• Keiichi Imato,
• Toshiaki Enoki,
• Koji Uenaka and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2019, 15, 1712–1721, doi:10.3762/bjoc.15.167

• ][18][19][20][21][22][23][24], and a promising photosensitizer for dye-sensitized solar cells (DSSCs) [25][26][27][28][29][30][31][32][33][34]. Thus, in this work, to gain insight into the photophysical and electrochemical properties of D–π–A fluorescent dyes with an azine ring as electron-withdrawing

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

• Yu-Ying Wang,
• Yong Kong,
• Zhe Zheng,
• Wen-Chao Geng,
• Zi-Yi Zhao,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

• materials and constructing dye-sensitized solar cells. Results and Discussion GC5A was prepared according to our previous procedure and represents a robust water-soluble macrocyclic receptor [26]. According to the positively charged feature of GC5A, a series of negatively charged dyes, including Fl, eosin Y

• bridge interactions, so the distance between the host and guest is too long for PET to occur. As well-known, Ru(II) complexes have been widely used in constructing dye-sensitized TiO2 solar cells [60]. The strong complexation between GC5A and Ru(dcbpy)3 provides an alternative way to non-covalently

• luminescent materials, high-performance supramolecular dye lasers, and dye-sensitized solar cells. Although in our present study GC5A has served as a specific test case for molecular recognition of various dyes, such an investigation is inspirable for other artificial receptors, especially those of new

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• complexes. These two types of metal-based complexes have been substantially developed in the last 40 years for different photochemical applications [40][41][42] and found wide applications in solar cells [43] or OLEDs (organic light-emitting devices) fabrication [44] and more recently in free radical

Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

• Akın Sağırlı and
• Yaşar Dürüst

Beilstein J. Org. Chem. 2018, 14, 3011–3017, doi:10.3762/bjoc.14.280

• crystals, and solar cells [7][8][9][10]. Taking into account the above considerations, new synthetic protocols to develop 1,2,4-oxadiazole-based heterocycles have gained an increasing attention over the recent decades [11][12][13]. On the other hand, arylacetonitriles are known as valuable intermediates

Metal-free formal synthesis of phenoxazine

• Gabriella Kervefors,
• Antonia Becker,
• Chandan Dey and
• Berit Olofsson

Beilstein J. Org. Chem. 2018, 14, 1491–1497, doi:10.3762/bjoc.14.126

• ][8], are present in a variety of dyes [9], and can be applied in chemosensors and dye-sensitized solar cells (Figure 1) [10][11][12]. N-Arylphenoxazines were recently employed as photoredox catalysts in metal-free polymerizations [13]. The first synthesis of phenoxazine dates back more than 100 years

Diels–Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

• Huangguan Chen,
• Jianwei Han and
• Limin Wang

Beilstein J. Org. Chem. 2018, 14, 354–363, doi:10.3762/bjoc.14.23

• °C resulted in N-phenylnaphthalen-1-ylamine (4) in 93% yield [23], which was widely used in dye-sensitized solar cells [24], hole transport materials [25][26] and organic light-emitting diodes (OLEDs, Scheme 2a) [27]. In another similar reaction with 3am, a novel N-phenylamine derivative 5 was

Regioselective decarboxylative addition of malonic acid and its mono(thio)esters to 4-trifluoromethylpyrimidin-2(1H)-ones

• Sergii V. Melnykov,
• Andrii S. Pataman,
• Yurii V. Dmytriv,
• Svitlana V. Shishkina,
• Mykhailo V. Vovk and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2017, 13, 2617–2625, doi:10.3762/bjoc.13.259

• Organofluorine compounds now play an essential role in the development of new materials for solar cells [1][2][3], radiotracers for PET imaging [4], agrochemicals [5][6], sensitive chemical probes for 19F nuclear magnetic resonance investigation of biological experiments [7][8], and are most widely used in the

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

• Jan Podlesný,
• Lenka Dokládalová,
• Oldřich Pytela,
• Adam Urbanec,
• Milan Klikar,
• Numan Almonasy,
• Tomáš Mikysek,
• Jaroslav Jedryka,
• Iwan V. Kityk and
• Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

• pigments [2], DPPs have significantly infiltrated organic electronics as functional dyes. The number of recently appeared review articles [3][4][5][6][7][8] clearly demonstrates their wide application potential, which spans organic solar cells (OSC), organic field-effect transistors (OFET), organic light

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• Phthalocyanines and subphthalocyanines are attracting attention as functional dyes that are applicable to organic solar cells, photodynamic therapy, organic electronic devices, and other applications. However, phthalocyanines are generally difficult to handle due to their strong ability to aggregate, so this

• novel material in the future. Besides blue organic pigments such as ink and colorants, it is expected to be widely applied to electronic devices in the medical field such as color filters for liquid crystal screens [12][13], storage media [14], dye-sensitized solar cells [15][16], photodynamic cancer

• for organic thin-film solar cells The introduction of trifluoroethoxy groups imparts not only a non-aggregation property and high solubility but also an electron-deficient π space and thermal or chemical stability to the phthalocyanine. For these reasons, it is expected that TFEO-Pcs will be developed

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• dots [107] and used as anchoring group for dye-sensitized solar cells [108][109][110] or for the immobilization of organocatalyst [111][112]. Phosphonic acid was also used for coating superparamagnetic iron oxide (e.g., magnetite) assessed as contrast agent in magnetic resonance imaging [113] or to

Molecular-level architectural design using benzothiadiazole-based polymers for photovoltaic applications

• Vinila N. Viswanathan,
• Arun D. Rao,
• Upendra K. Pandey,
• Arul Varman Kesavan and
• Praveen C. Ramamurthy

Beilstein J. Org. Chem. 2017, 13, 863–873, doi:10.3762/bjoc.13.87

• OPV devices led to a new type of device, the so-called bulk heterojunction (BHJ) solar cells, with improved power-conversion efficiency (PCE) [2][3][4]. A large number of polymer semiconducting materials of donor–acceptor–donor (D–A–D) architecture have been synthesized and used in OPV devices

• OPVs based on bulk heterojunction (BHJ) solar cells of polymers P1, P2 and P3 and tested them with PC70BM as an acceptor. The device architecture of the BHJ solar cell was ITO/PEDOT:PSS (40 nm)/polymer:PC70BM (120 nm)/Ca (15 nm)/Al (100 nm). Figure 6 shows the favorable energy alignments for both

• obtained. The active layer morphology in polymer solar cells is crucial and can drastically affect the performance of the devices. For optimum performance of an OPV device, the phase-separated donor and acceptor domain sizes should be twice the exciton diffusion length, which is typically of the order of 7

Effects of solvent additive on “s-shaped” curves in solution-processed small molecule solar cells

• John A. Love,
• Shu-Hua Chou,
• Ye Huang,
• Guilllermo C. Bazan and
• Thuc-Quyen Nguyen

Beilstein J. Org. Chem. 2016, 12, 2543–2555, doi:10.3762/bjoc.12.249

• , National Taiwan University, Taipei, 10617, Taiwan 10.3762/bjoc.12.249 Abstract A novel molecular chromophore, p-SIDT(FBTThCA8)2, is introduced as an electron-donor material for bulk heterojunction (BHJ) solar cells with broad absorption and near ideal energy levels for the use in combination with common

• separation. This yields much better performing devices, with improved curve shape, demonstrating the importance of morphology control in BHJ devices and improving the understanding of the role of solvent additives. Keywords: current voltage analysis; morphology; organic solar cells; Introduction Tremendous

• multidisciplinary research efforts have led to consistent increases in the efficiency of organic solar cells, making the technology a bright prospect in the quest for alternative energy [1][2][3][4]. In particular the rapid development of solution-processed small molecule materials over the last several years has