Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• fluorescent chemosensors and probes [4][5][6], as well as materials for applications in organic light-emitting diodes (OLEDs) [7][8][9], organic field-effect transistors (OFETs) [10], and perovskite solar cells [11]. In this respect, replacing either one or more of the carbons or rings of a fluoranthene with

The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• p-type semiconductors with low HOMO–LUMO gaps (≈1.25 eV). The hole mobilities, measured from fabricated organic field-effect transistors, range from 3.6 × 10−6 to 1.0 × 10−2 cm2 V−1 s−1. We found that the compounds featuring linear alkyl chains (3b and 3c) displayed a higher mobility compared to the

• field-effect transistor; organic semiconductor; violanthrone; Introduction Recently, organic semiconductors have received considerable attention due to their potential technological applications in semiconductor devices, such as organic field-effect transistors (OFETs) [1][2], organic light-emitting

• transistors (OFETs) fabrication and measurement Bottom-gate, bottom-contact organic field-effect transistors were made using prefabricated substrates (Fraunhofer IPMS, product code 1301). The substrates consisted of an n-doped Si gate electrode, SiO2 (230 nm) dielectric layer and Au (30 nm + 10 nm ITO

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

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• molecules; N-heteroacenes; hydrogen bonding; optoelectronic properties; organic field-effect transistors; organic semiconductors; Introduction The role of weak intermolecular interactions in tuning the properties of organic semiconductors has garnered significant attention in the past two decades, owing to

Organic electron transport materials

• Joseph Cameron and
• Peter J. Skabara

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

• semiconductor layer of n-type organic field-effect transistors. Typically, an electron transport material should have a high electron mobility and a low-lying lowest unoccupied molecular orbital (LUMO) relative to vacuum. This is achieved by using electron-deficient units containing highly electronegative

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• -conjugated polycyclic compounds appeared as particularly valuable in this field. Indeed, many of them demonstrated excellent performances as active components of electronic devices such as organic field effect transistors (OFETs), organic photovoltaic cells (OPVs) and organic light-emitting diodes (OLEDs

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

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

• ), organic field-effect transistors (OFETs), organic-light emitting diodes (OLEDs) and other organic electronic technologies. Notably, the potential of quinoxaline derivatives as non-fullerene acceptors in OSCs, auxiliary acceptors and bridging materials in DSSCs, and n-type semiconductors in transistor

• 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

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

• wavelength is at 701 nm, which corresponds to 1.77 eV. An ionisation energy of 5.5 eV and an electron affinity of 3.3 eV were estimated by cyclic voltammetry measurements. We have applied this new molecule in organic field effect transistors. The material exhibited a p-type mobility up to 1.33 × 10−4 cm2 V−1

• -deficient keto groups. Interestingly, neither the HOMO, nor the LUMO, is present at the central sulfur atom of the DTT motif. Organic field-effect transistors To estimate the charge carrier mobility from the saturation regime of the current–voltage plot, bottom gate/bottom contact (BG/BC) OFETs [76][77

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

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

• , anti-Kasha photophysics, and a small HOMO–LUMO gap when compared to its isomer, naphthalene. These properties make azulene-containing polymers an intriguing entity in the field of functional polymers, especially for organic electronic applications like organic field-effect transistors (OFET) and

• 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

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

• application of several organic materials, such as organic light-emitting diodes (OLEDs) [5], organic field-effect transistors (OFETs) [6], polymeric materials [7], and other kinds of materials [8][9][10]. For example, OLEDs fabricated with 9,10-diphenylanthracene derivatives 1 and 2 are blue light emitters

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

• introduction of the second isoindigo fragment is indicated by an arrow, Scheme 21). However, the efficiency of the cell based on the monoindigo derivative turned out to be slightly higher (2.66 vs 2.50%). Isoindigo as the basis for organic field-effect transistors (OFET) In recent years, the interest of

Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings

• Ivan P. Mosiagin,
• Olesya A. Tomashenko,
• Dar’ya V. Spiridonova,
• Mikhail S. Novikov,
• Sergey P. Tunik and
• Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2021, 17, 1490–1498, doi:10.3762/bjoc.17.105

• potentially useful material for organic field-effect transistors [1]. Bases 6 can be easily methylated and benzylated on the pyrrole nitrogen with formation of the corresponding salts N-Me-and N-Bn-3a in quantitative yield (Scheme 5). Encouraged by the above mentioned results we decided to apply the developed

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

• [22][27], organic field-effect transistors [28], or sensors [23]. The interesting structure–property relationships of the S,N-heteroacene series inspired as well theoretical work. In this respect, De Simone et al. computed electronic spectra of the neutral, charged radical cationic, and dicationic

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

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

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

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

• transistors (OFETs) [35][36], and other optoelectronic devices. Our approach to C3-symmetric molecules containing propellane moieties involve DA reaction [37], cyclotrimerization [19] and RCM [38][39][40][41] as key steps. Results and Discussion The synthesis of propellane-bearing C3-symmetric derivatives

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

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 photophysical properties of novel benzophospholo[3,2-b]indole derivatives

• Mio Matsumura,
• Mizuki Yamada,
• Atsuya Muranaka,
• Misae Kanai,
• Naoki Kakusawa,
• Daisuke Hashizume,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

• ; photophysical property; Introduction The chemistry of phospholes, fully unsaturated five-membered heterocyclic rings containing a phosphorus element, has drawn much attention in terms of the development of synthetic methods and elucidation of its spectroscopic properties for applications in organic field

• -effect transistors (OFETs) and luminescent materials [1][2][3][4][5][6][7][8][9]. The phosphorous atom of trivalent phosphorus compounds has a high chemical reactivity. Therefore, several reactions on the phosphorus atom such as oxidation, alkylation, and coordination to a Lewis acid can produce the

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

• Roman A. Irgashev,
• Nikita A. Kazin,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136

• -dihydroindolo[3,2-b]carbazole (indolo[3,2-b]carbazole, ICZ) has been successfully used as a basic structural fragment of perspective electroluminescent, hole-transporting materials and light-harvesting dyes for organic light emitting diodes (OLEDs) [7][8][9][10][11][12][13], organic field-effect transistors

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

• hole-transport materials in organic light emitting diodes [10][11][12][13][14][15], organic field-effect transistors [16][17][18][19][20][21][22], and organic photovoltaics [23][24][25][26]. Likewise their smaller congeners, 2,5-di(hetero)aryl substituted thiophenes [4][5], are equally relevant as