Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra

• Yuuki Ishii,
• Minoru Yamaji,
• Fumito Tani,
• Kenta Goto,
• Yoshihiro Kubozono and
• Hideki Okamoto

Beilstein J. Org. Chem. 2025, 21, 670–679, doi:10.3762/bjoc.21.53

• molecules in spite of their long history; phenacenes were recognized as contents in petroleum-industry residues as early as in the 19th century [8][9]. In the last decade, phenacenes were demonstrated to serve as platform materials namely in organic electronics, such as chromophores for photovoltaics [10

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• ][12][13]. The most promising applications of truxene-based systems have been found in organic photovoltaics (OPVs), dye‐sensitized solar cells (DSSCs), fluorescent probes, organic thin‐film transistors (OTFTs), lasers, organic light emitting diodes (OLEDs), liquid crystals, non-linear optical (NLO

Hetero-polycyclic aromatic systems: A data-driven investigation of structure–property relationships

• Sabyasachi Chakraborty,
• Eduardo Mayo Yanes and
• Renana Gershoni-Poranne

Beilstein J. Org. Chem. 2024, 20, 1817–1830, doi:10.3762/bjoc.20.160

• molecules have been used in diverse settings, functioning as organic field effect transistors [10][11][12], light-emitting diodes [13][14][15], organic semiconductors [16][17], organic photovoltaics [1][18][19][20][21][22], photocatalysts [23], and biological agents for tracking or inhibition [24][25], and

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

• Yong-Chang Zhai,
• Shimon Oiwa,
• Shinobu Aoyagi,
• Shohei Ohno,
• Tsubasa Mikie,
• Jun-Zhuo Wang,
• Hirofumi Amada,
• Koki Yamanaka,
• Kazuhira Miwa,
• Naoyuki Imai,
• Takeshi Igarashi,
• Itaru Osaka and
• Yutaka Matsuo

Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109

• (FIDO, FIDS, C60) as electron-acceptors were compared, and the open-circuit voltage with FIDS was 0.16 V higher than that with C60. Keywords: C60; evaporable fullerene derivatives; organic photovoltaics; organic solar cells; thioketone; Introduction Fullerene is a carbon allotrope that has attracted

• significant scientific interest since its discovery by H. W. Kroto in 1985 [1]. Due to their distinctive spherical structure and electron-deficient properties, fullerene derivatives have found applications in various fields, including photovoltaics [2][3][4][5], biomedicine [6][7][8], and electron

Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C₇₀ production

• Cristina Castanyer,
• Anna Pla-Quintana,
• Anna Roglans,
• Albert Artigas and
• Miquel Solà

Beilstein J. Org. Chem. 2024, 20, 272–279, doi:10.3762/bjoc.20.28

• holds significant promise for applications in the fields of medicinal chemistry, materials science, and photovoltaics. In this study, we investigate the regioselectivity of the rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions between diynes and C70 as a novel procedure for generating C70 bis

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• tinctoria plant. Like indirubins, the isoindigo derivatives were initially studied as potential therapeutics with pronounced antitumor activity [74]. More recently, advantageous charateristics of isoindigos for the applications in organic photovoltaics (OPV) [75] and optoelectronics [76] were revealed. The

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• Sciences, Beijing, China 10.3762/bjoc.20.8 Abstract Large donor–acceptor scaffolds derived from polycyclic aromatic hydrocarbons (PAHs) with tunable HOMO and LUMO energies are important for several applications, such as organic photovoltaics. Here, we present a large selection of PAHs based on central

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• ; columnar liquid crystal; organic electronics; perylene; pyrene; Introduction Conjugated organic molecules have been widely investigated due to their interesting transport properties and promising applications as active layer in organic photovoltaics (OPVs), organic field effect transistors (OFETs

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

• ethyl acetate, while using a bulk heterojunction (BHJ) comprised of PM6:Y6. High power conversion efficiencies (PCEs) of 13% were achieved compared to control devices using the standard PFN-Br CIL. Keywords: cathode interlayer materials; green solvent processing; organic photovoltaics; Introduction

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

• reaction conditions and gives higher yields of product than directly linked azido or alkynyl porphyrins. Many applications for porphyrin click products have been proposed, including chemical sensing, anion-binding affinity, photovoltaics devices, light-harvesting materials, and in the synthesis of water

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

• Hengjia Liu and
• Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

• ][32], e.g., organic thin-film transistors [45][46], organic photovoltaics [47], and chemical sensing [48]. Chemical structures of Lewis acid examples. Chemical structures of Lewis basic fluorescent polymer poly{2,5-pyridylene-co-1,4-[2,5-bis(2-ethylhexyloxy)]phenylene} 1 and D–A–D compound 2,5-bis((N

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

• 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

• photovoltaics can be found in the form of derivatives 28 and 29, containing two differently substituted isoindigo fragments connected through a thienylene spacer (Scheme 16). Bini et al. described the synthesis of polymer series 28a–e with different ratios of isoindigo fragments, one of which is capable of

• may be due to the low hole conductivity, a decrease in the HOMO level of the polymer, and a narrower band gap of visible light absorption [51]. Within the framework of the study of the prospects for polymer derivatives of isoindigo in organic photovoltaics and avoiding the use of the fullerene

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

Dawn of a new era in industrial photochemistry: the scale-up of micro- and mesostructured photoreactors

• Emine Kayahan,
• Mathias Jacobs,
• Leen Braeken,
• Leen C.J. Thomassen,
• Simon Kuhn,
• Tom van Gerven and
• M. Enis Leblebici

Beilstein J. Org. Chem. 2020, 16, 2484–2504, doi:10.3762/bjoc.16.202

Synthesis of 6,13-difluoropentacene

• Matthias W. Tripp and
• Ulrich Koert

Beilstein J. Org. Chem. 2020, 16, 2136–2140, doi:10.3762/bjoc.16.181

• expanded π-systems and low HOMO–LUMO gaps with applications in different molecular-based organic electronics like OFETs, OLEDs or organic photovoltaics [1][2][3]. An advantage of organic molecular electronics over inorganic alternatives is the versatility in design of new molecular materials by

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

• sustainable photovoltaics [102], flexible electronics [103], improved organic light emitting diodes (OLEDs) [104], organic field effect transistors (OFETs) [105][106], and more recently, photocatalysts [3][5][10][15]. These materials have semiconducting properties due to extended conjugation producing a

• problematic for photovoltaics and photocatalysts but a useful property for OLEDs where the radiative decay of the charge recombination is desired [112][114]. Charge carriers are normally localised to only a few atoms and cause large distortions in the local electronic structure. This small spatial confinement

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

• , respectively. Keywords: carbazole; electrochemistry; fluorescence; formyl group; solvatochromism; Introduction Carbazole derivatives have found many different applications in a variety of technologically important areas, such as organic light emitting diodes (OLEDs), organic photovoltaics (OPVs), dye

Synthesis of dipolar molecular rotors as linkers for metal-organic frameworks

• Sebastian Hamer,
• Fynn Röhricht,
• Marius Jakoby,
• Ian A. Howard,
• Xianghui Zhang,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1331–1338, doi:10.3762/bjoc.15.132

• acid 1 using cesium fluoride under a carbon dioxide atmosphere. Difluoro- and dicyanobenzothiadiazole compounds 2 and 3 Substituted benzothiadiazole derivatives are well studied in the literature and are of great interest in organic photovoltaics and electronics. As there are no reports of such

Extending mechanochemical porphyrin synthesis to bulkier aromatics: tetramesitylporphyrin

• Qiwen Su and
• Tamara D. Hamilton

Beilstein J. Org. Chem. 2019, 15, 1149–1153, doi:10.3762/bjoc.15.111

• catalysis [1], photovoltaics [2], photodynamic therapy [3][4], environmental remediation [5][6], biomimetic modelling [7] and metal-organic self-assembly [8]. Porphyrins may be substituted in the meso or β-positions (Figure 1A). Tetra-meso-substituted porphyrins are usually synthesized from simple starting

Synthesis of C₃-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step

• Sambasivarao Kotha and
• Saidulu Todeti

Beilstein J. Org. Chem. 2019, 15, 371–377, doi:10.3762/bjoc.15.33

• trimers and synthetic access to such amino acids is vital. In this regard, new star-shaped C3-symmetric molecules [16][17][18][19][20][21][22][23][24][25][26] have been used in photovoltaics [27][28], organic light-emitting diodes (OLEDs) [29][30], organic field-effect transistors (OFETs) [31][32] and

Olefin metathesis in multiblock copolymer synthesis

• Maria L. Gringolts,
• Yulia I. Denisova,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21

• attract ongoing attention from both experimentalists and theoreticians due to their intrinsic tendency to self-assemble into diverse microstructures [8][9][10][11]. Technological applications of block copolymers cover lithography [12], photovoltaics [13], membranes [14] and many other areas [15]. Most of

Design and synthesis of C₃-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

• Sambasivarao Kotha,
• Saidulu Todeti and
• Vikas R. Aswar

Beilstein J. Org. Chem. 2018, 14, 2537–2544, doi:10.3762/bjoc.14.230

• -symmetric molecules [19][20][21][22][23][24][25][26][27][28][29][30], here, we conceived new strategies to N-containing star-shaped molecules. Such star-shaped molecules are generally used in organic light-emitting diodes (OLEDs) [31][32][33], organic photovoltaics (OPVs) [34], organic field-effect

Synergistic electrodeposition of bilayer films and analysis by Raman spectroscopy

• Saadeldin E. T. Elmasly,
• Luca Guerrini,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Neil J. Findlay,
• Karen Faulds and
• Peter J. Skabara

Beilstein J. Org. Chem. 2018, 14, 2186–2189, doi:10.3762/bjoc.14.191

• bilayer to be subjected to solution-processing. It is therefore possible to deposit any layer onto the neutral insoluble polymer (e.g., an acceptor material for organic photovoltaics or an electron transport material for OLEDs) illustrating the potential for electrochemically deposited bilayers to be used

Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

• Thanh-Tuân Bui,
• Fabrice Goubard,
• Malika Ibrahim-Ouali,
• Didier Gigmes and
• Frédéric Dumur

Beilstein J. Org. Chem. 2018, 14, 282–308, doi:10.3762/bjoc.14.18

Synthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds

• Baris Temelli and
• Hilal Kalkan

Beilstein J. Org. Chem. 2018, 14, 187–193, doi:10.3762/bjoc.14.13

• as good candidates for many important applications ranging from photovoltaics to medicine. 1H NMR spectrum of 4a in CDCl3. Overview of the synthesis of directly linked porphyrin–corrole hybrid compounds. Synthesis of β-meso directly linked porphyrin–corrole hybrid compounds. Synthesis of porphyrin