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

• will be useful in summarizing the advances and challenges as well as provide a platform for new scientific ideas and discoveries that will promote the applications of photochromic indigo derivatives in various fields from materials science and organic electronics to biology and medicine. Precursors

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

• ; Introduction In recent years, organic electronics have become very attractive due to their various advantages such as high flexibility, easy designability, low fabrication cost, easy processing and large-scale fabrication [1][2][3][4]. Especially in display technology, organic-based materials have found use in

• many applications such as OLEDs, micro-LEDs, LCDs, lasers, and photodiodes by applying thin film methods and solution processes [5][6][7][8]. The performance of organic electronics is based on the active layer composition as well as the fabrication methods and processing parameters. The organic active

• properties indicated that the composition of thienothiophene, triphenylamine, and boron is a highly suitable combination for fluorescent organic electronics in display technology. Experimental General methods 1H and 13C NMR spectra were recorded on a Varian model NMR spectrometer (500 and 126 MHz) and

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

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

• transport applications. Furthermore, ongoing research efforts aimed at enhancing their performance and addressing key challenges in various applications are presented. Keywords: electron transport materials; non-fullerene acceptors; n-type semiconductors; organic electronics; quinoxalines; Introduction

• based on Qxs is of significant interest in the field of organic electronics. A compelling indication of this potential is the remarkable achievements made by a relatively simple polymer, poly[(thiophene)-alt-(6,7-difluoro-2-(2-hexyldecyloxy)quinoxaline)] (PTQ10). PTQ10 has demonstrated impressive power

• and optimization, Qx polymer acceptors are expected to evolve into high-performance materials for organic electronics. Quinoxalines as NFAs Fullerene acceptors have long dominated OSCs until the emergence of NFAs; nonetheless, researchers have attempted to improve fullerenes and address their

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite’s conformance

• Ruslan P. Shekurov,
• Mikhail N. Khrizanforov,
• Ilya A. Bezkishko,
• Tatiana P. Gerasimova,
• Almaz A. Zagidullin,
• Daut R. Islamov and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1499–1504, doi:10.3762/bjoc.18.157

• properties. Such switchable systems with conjugated organic fragments containing an FeII/FeIII system were used in organic electronics as molecular switches, optoelectronic materials and in biochemistry as photonic or redox devices [6]. A promising approach is the coordination self-assembly of multiferrocene

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 2450–2461, doi:10.3762/bjoc.17.162

• organic molecules are finding use in numerous areas ranging from organic electronics [1][2][3][4][5], ions sensing [6][7], and solar cell development [8][9][10]. Within this background, acridines represent an interesting class of heteroaromatic π-conjugated compounds [11][12][13][14] which show great

• perspectives in medicinal chemistry [15][16][17][18][19][20][21][22][23], dye industries [24][25][26], and metal chemo sensing [27][28][29]. More recently, acridines have received growing attention in organic electronics [30][31][32], due to their strong electron-donating ability [33][34] and remarkable

Chemical syntheses and salient features of azulene-containing homo- and copolymers

• Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

• -containing homo- and copolymers, including brief descriptions of their key properties. Keywords: azulene; chemical synthesis; copolymer; non-alternant hydrocarbon; organic electronics; polyazulene; Introduction Azulene (C10H8) is a non-alternant, non-benzenoid, 10 π electron aromatic hydrocarbon containing

• synthesis of functional polymers is also an interesting proposition and such polymers can find promising applications in the organic electronics field such as organic field-effect transistors (OFET) and photovoltaic (PV) cells [15][16]. The synthesis of azulene-containing polymers can be envisaged through

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

• Ranadeep Talukdar

Beilstein J. Org. Chem. 2021, 17, 2102–2122, doi:10.3762/bjoc.17.137

• broad applications in organic electroluminescent devices [44]. Silanes Heteroaryl compounds containing silicon, an earth abundant and non-toxic element, are important in organic electronics or photonics and in the field of drug discovery and nuclear medicine [45][46][47][48][49][50]. The first property

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

• researchers in semiconductor materials has covered the field of organic electronics. The advantages of organic oligomeric and polymeric materials for applications in OFET and thin-film transistor (TFT) technologies are due to the ease of their directed chemical modification, mechanical flexibility, the

• considerable interest of researchers in the field of organic electronics [92][93][94]. Isoindigo derivatives have similar characteristics. Taking into account these data, copolymers 51 containing up to 25% DPP units were obtained [95]. Despite the good prerequisites, an OFET based on this copolymer showed only

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

• Mio Matsumura,
• Takahiro Teramoto,
• Masato Kawakubo,
• Masatoshi Kawahata,
• Yuki Murata,
• Kentaro Yamaguchi,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2021, 17, 671–677, doi:10.3762/bjoc.17.56

• functional π-electron materials for organic electronics applications is under progress, and the results will be reported in due time. Benzonaphthophosphindoles. Crystal structure of 2: different views. a) Absorption spectra and b) normalized fluorescence spectra for selected compounds in CHCl3. The spatial

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

• application in organic electronics. Results and Discussion Synthesis of N-alkylated S,N-heterotetracene 9 by Pd-catalyzed amination. Asymmetric S,N-heterotetracene Hex-SN4 9 comprises the sequence of heteroatoms ‘SSNS’ in the tetracyclic conjugated π-system [37]. In a multistep synthesis, 2,6

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

• photocatalytic decomposition of water on illuminated titanium dioxide (TiO2) electrodes in 1972 [27]. This critical report began the field of semiconductor HPC, and in combination with the development of organic electronics, established fundamental principles that still underpin much of the cutting-edge

• electrostatic repulsion that prevents the dye adsorption. 2.2 Organic semiconductor photocatalysis Polyaniline was the first conductive polymer reported by Henry Letheby in 1862 [99][100], but the potential of organic electronics was not realised until the 1960s, and the seminal work of Heeger, MacDiarmid, and

• Shirakawa, leading to their shared award of the 2000 Chemistry Nobel Prize for “the discovery and development of conductive polymers” [101]. For the following 60 years, and still to this day, organic electronics is a vibrant field of research within materials chemistry and physics as a potential source of

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

• , Turkey WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, G128QQ Glasgow, UK 10.3762/bjoc.16.93 Abstract Two novel carbazole-based compounds 7a and 7b were synthesised as potential candidates for application in organic electronics. The materials were fully characterised by NMR

Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

• Md. Shafiqur Rahman and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2020, 16, 524–529, doi:10.3762/bjoc.16.48

• extended π-system. These included, in particular, those fused with polycyclic aromatic hydrocarbons (PAHs) for possible applications in organic electronics, bioimaging and sensing, and asymmetric catalysis (Figure 1). To name a few examples, Yamaguchi et al. described synthetic routes to novel phosphorus

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

• ]thiophene; thieno[2',3':4,5]thieno[3,2-b]indole; Introduction The thieno[3,2-b]thiophene (TT) unit is highly demanded in modern organic synthesis since TT-based compounds have a variety of applications, e.g., in the field of organic electronics. Indeed, TT-based polymers and small molecules are used as

Naphthalene diimides with improved solubility for visible light photoredox catalysis

• Barbara Reiß and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 2043–2051, doi:10.3762/bjoc.15.201

• self-assembly [43][44], as molecular sensors [45][46][47] and for organic electronics [48][49], but yet nearly completely unexplored for photoredox catalysis. Core-unsubstituted NDIs are colorless compounds with high extinction coefficients at the border between UV-A and visible light. Their

Atom-economical group-transfer reactions with hypervalent iodine compounds

• Andreas Boelke,
• Peter Finkbeiner and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108

• organic electronics and can be obtained in good yields and an AE of 48% (Ar1 = p-Tol, Ar2 = Ar3 = Ph) using this Cu(I)-catalysed domino approach. The formation of an intermediately found diarylaniline supposedly follows a Cu(I)/Cu(III) cycle, whereas a radical mechanism is proposed for the second

Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

• Fabiana Pandolfi,
• Isabella Chiarotto and
• Marta Feroci

Beilstein J. Org. Chem. 2018, 14, 891–899, doi:10.3762/bjoc.14.76

• (1b, Scheme 8). In fact, the corresponding alkyne 2b is an important intermediate in the synthesis of molecules for organic electronics (e.g., organic light-emitting diodes [33] and organic field-effect transistors [34]). The voltammetric analysis showed a behavior similar to that of 1a (see

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

• investigated in organic electronics [31] as these materials are characterized by a remarkable electron mobility resulting from the presence of a vacant p-orbital on the boron atom [32][33]. Triarylboron compounds are also strong electron acceptors, justifying that numerous groups developed TADF emitters using

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• characterized environment-dependent fluorescence. This property, together with the facile synthetic accessibility, makes it and its derivatives useful for a number of applications, e.g., as materials for organic electronics [1], dyes for mechanochromic materials [2], and fluorescent monomers for polymer

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

Interactions between shape-persistent macromolecules as probed by AFM

• Johanna Blass,
• Jessica Brunke,
• Franziska Emmerich,
• Cédric Przybylski,
• Vasil M. Garamus,
• Artem Feoktystov,
• Roland Bennewitz,
• Gerhard Wenz and
• Marcel Albrecht

Beilstein J. Org. Chem. 2017, 13, 938–951, doi:10.3762/bjoc.13.95

• ][3][4]. Especially shape-persistent polymers are of significant scientific interest as their defined structural characteristics offer various applications as sensor materials, biomimetic filaments or organic electronics [5][6][7]. Furthermore, compared to polymers with flexible chains, shape

Fast and efficient synthesis of microporous polymer nanomembranes via light-induced click reaction

• Qi An,
• Youssef Hassan,
• Xiaotong Yan,
• Peter Krolla-Sidenstein,
• Tawheed Mohammed,
• Mathias Lang,
• Stefan Bräse and
• Manuel Tsotsalas

Beilstein J. Org. Chem. 2017, 13, 558–563, doi:10.3762/bjoc.13.54

• storage and separation as well as in organic electronics [8]. Among the microporous materials, conjugated microporous polymers (CMPs) [9][10] or porous aromatic frameworks (PAF) [11] have favorable properties for many applications, since they combine a high chemical and thermal stability, which is

• virtually any support, allows the integration of TYC based CMP materials in functional devices for applications in organic electronics or gas and liquid phase separation. Experimental Chemicals: All chemicals were purchased from commercial sources and used without further purification if not stated