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

• 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

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

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

• 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

• -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

• various acids [49]. This system is completely metal-free and uses one photocatalyst rather than separate sensitizer and catalyst species. However, the electron source for the reductions was a thiolate sacrificial donor and not water. Thiolates are used as redox mediators in other systems such as dye

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

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

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

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

• 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

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 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

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

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

• 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

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

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

• 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

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

Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

• Dominik Urselmann,
• Konstantin Deilhof,
• Bernhard Mayer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2016, 12, 2055–2064, doi:10.3762/bjoc.12.194

• -transfer characteristics [59][60][61][62][63], as hole-transport materials [64], for applications in mesoporous organo silica hybrid materials [65], and as chromophores in dye-sensitized solar cells [66][67][68]. Furthermore, (oligo)phenothiazines in their native reduced forms display a pronounced ability

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

• Wei Li,
• Munechika Otsuka,
• Takehito Kato,
• Yang Wang,
• Takehiko Mori and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

• the PCE of 4% [1], some key improvements have been made in designing device structures and fabrication methods, and the PCE of the PSCs rapidly increased to >20% [2][3][4][5]. Compared to the conventional organic photovoltaics and dye-sensitized solar cells (DSSCs), PSCs benefit from a broad light

Indenopyrans – synthesis and photoluminescence properties

• Andreea Petronela Diac,
• Ana-Maria Ţepeş,
• Albert Soran,
• Ion Grosu,
• Anamaria Terec,
• Jean Roncali and
• Elena Bogdan

Beilstein J. Org. Chem. 2016, 12, 825–834, doi:10.3762/bjoc.12.81

• chromophores are valuable candidates for the fabrication of OLEDs [21][22], dye lasers [23], sensors [24], dye-sensitized solar cells, fluorescent probes [25] or logic gates [26]. Recently [27], 6-CF3-2H-pyran-2-ones have been reported as potential building blocks for the preparation of novel

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• attention of chemists and physicists on high electrical conductivity and superconductivity with high Tc temperature. Recently, however, TTF and its derivatives are frequently employed as a redox-active moiety for organic electronic devices such as field-effect-transistors (FET), dye-sensitized solar cells

A hybrid electron donor comprising cyclopentadithiophene and dithiafulvenyl for dye-sensitized solar cells

• Gleb Sorohhov,
• Chenyi Yi,
• Michael Grätzel,
• Silvio Decurtins and
• Shi-Xia Liu

Beilstein J. Org. Chem. 2015, 11, 1052–1059, doi:10.3762/bjoc.11.118

• HOMO–LUMO gap. In turn, the direct linkage of D and A units leads to an effective π-conjugation, thus substantially lowering the HOMO–LUMO gap. Moreover, the application in dye-sensitized solar cells was investigated, showing that the power conversion efficiency increases by the insertion of the phenyl

• unit. Keywords: donor–acceptor systems; dye-sensitized solar cells; electrochemistry; intramolecular charge transfer; Knoevenagel reaction; tetrathiafulvalene; Introduction Dye-sensitized solar cells (DSSCs) have been intensively investigated as an alternative to silicon-based solar cells [1][2][3][4

• spacer. As a consequence, the direct linkage of the D and A units leads to an effective π-conjugation, thus substantially lowering the HOMO–LUMO gap and increasing the light-harvesting ability. The application in dye-sensitized solar cells was further investigated, showing that the power conversion

A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles

• Roman A. Irgashev,
• Arseny A. Karmatsky,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2015, 11, 1000–1007, doi:10.3762/bjoc.11.112

• compounds which can be applied in organic optoelectronic materials. Indeed, we have recently reported the synthesis of novel push–pull dyes IK-1,2 based on the thieno[2,3-b]indole ring system, as a donating part of dye-sensitized solar cells [8] (Figure 1). It should be noted that thieno[2,3-b]pyrrole and

• analogues. This two-step approach provides an easy access to compounds of the family of electron-rich thieno[2,3-b]indoles, which are regarded as promising building-blocks for the development of new photo- and electrosensitive molecules, e.g., novel push–pull dyes for dye-sensitized solar cells