Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• , compound 7 is characterized by electron transport. The recorded current transients for electrons in vacuum-deposited films of compound 7 show moderate dispersion (Figure 8a). In contrast, the hole transport was not detected, apparently because of the low mobility of holes being out of the detectable range

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

• conventional device architecture of ITO/PEDOT:PSS/TFB/TAPC:TCTA:emitter (DMB-TT-TPA (8))/TPBi/LiF/Ca/Ag, where TFB, TCTA/TAPC, and TPBi acted as hole transport, hole transporting host, and electron transport materials, respectively (Figure S2 in Supporting Information File 1). The current efficiency–luminance

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

• , 33600 Pessac, France 10.3762/bjoc.19.128 Abstract Electron and hole transport characteristics were evaluated for perylene-based and pyrene-based compounds using electron-only and hole-only devices. The perylene presented a columnar hexagonal liquid crystal phase at room temperature with strong

• . While 1 presents majority hole transport, 2 is moderately ambipolar. The electron transport of 2 is around two orders of magnitude higher than 1, which can be associated to the larger conjugation of 2. This work highlights the potential of pyrene-based columnar liquid crystals as electron-transporting

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

• materials further enhances the practicality and commercial viability of Qxs for charge transport applications [6][7][8][9][10]. Figure 1 shows a few Qx scaffolds used in development of Qx derivatives. The utilization of Qxs as a charge transporting material, whether as a hole transport material (HTM) or an

• electron transport material (ETM), is largely dependent on its functionalization. Although the Qx material has primarily been recognized for its effectiveness in hole transport, several studies have unveiled its significant potential as an ETM [6][7][11][12], exhibiting desirable characteristics such as

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• at 440 nm [64], TCTA at 410 nm [65], and TPBi at 390 nm [66]) and at longer wavelengths due to the excimer/exciplex emissions at the interfaces of NPB-TCTA/EML and EML/TPBi were observed, signifying that the OLED possessed a well-balanced electron and hole transport. Moreover, due to the efficient

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

• candidates as they can form electron transporting films, have appropriate LUMO energy levels compatible with most photoactive acceptor molecules (LUMO levels residing between −3.5 eV to −4.0 eV) to promote electron cascade, have appropriate HOMO energy levels at −5.5 eV and below that serve to block hole

• transport, exhibit high thermal stability, are highly tunable in terms of their physical and chemical properties, and can be readily doped thereby increasing electronic conductivity. Some of the most widely used PDI materials for CILs are PDIN [14], PDINN [15], and PDINO (Figure 1a) [14][15]. Past work in

Molecular and macromolecular electrochemistry: synthesis, mechanism, and redox properties

• Shinsuke Inagi and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 1505–1506, doi:10.3762/bjoc.18.158

• of organic electrochemistry for energy material applications. Organic semiconductor design for electron or hole transport is important for transistor and solar cell applications, and redox-active (but stable) organic and polymeric materials are promising for secondary batteries and redox flow

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

• -mediated reaction of bisindole derivative 32 with Ph2SiCl2 (33, Scheme 5b) [56]. The dissociation of the indole C-2–Si bond upon UV light excitation generates a hole transport layer (HTL) in these materials, facilitating the optical activity [57]. In 1996, Frenzel reported the synthesis of bis(indol-3-yl

D–A–D-type orange-light emitting thermally activated delayed fluorescence (TADF) materials based on a fluorenone unit: simulation, photoluminescence and electroluminescence studies

• Lin Gan,
• Xianglong Li,
• Xinyi Cai,
• Kunkun Liu,
• Wei Li and
• Shi-Jian Su

Beilstein J. Org. Chem. 2018, 14, 672–681, doi:10.3762/bjoc.14.55

• donors in TADF materials, has strong electron-donating and hole-transport ability. The combination of the strong acceptor and strong donor can give a narrow energy gap and thus longer wavelength emission. Compounds 1 and 2 were thoroughly characterized by 1H NMR, 13C NMR and electron ionization (EI) mass

• % emitter in CBP (35 nm)/TmPyPB (55 nm)/LiF (1 nm)/Al, where 1,1-bis(4-(di-p-tolylamino)phenyl)cyclohexane (TAPC), 4,4'-bis(9H-carbazol-9-yl)biphenyl (CBP), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene (TmPyPB) and LiF play the roles of hole transport layer, host material, electron transport layer and electron

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

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

• -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

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• method was described in detail in our previous paper [34]. The hole transport mobilities of COOP-nHT-TBDT were measured to be 2.01 × 10−6, 1.81 × 10−6, 4.60 × 10−4 and 8.22 × 10−4 cm2·V−1·s−1 for 1, 2, 3, and 4, respectively. Obviously, the largest molecule 4 displays the highest hole mobility, which

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

• ; hole transport; perovskite solar cell; polycondensation; Introduction Inorganic–organic hybrid perovskite solar cells (PSCs) have recently received significant attention due to their remarkably high power convention efficiencies (PCEs). After the seminal study reported by Miyasaka et al. in 2009 with

• absorption by the hole-transporting polymers does not significantly contribute to the photocurrent generation and the main role of the polymers is hole transport. The peak intensities of the IPCE spectra obtained from the devices based on 3,6-Cbz-EDOT and 2,7-Cbz-EDOT exceeded 0.70 in the wavelength range of

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

• thieno[3,2-b]pyrrole ring systems have been incorporated in the structures of various fused polycyclic compounds (heteroacenes), which have been used as efficient hole-transport materials for organic light emitting diodes (OLEDs) or field effect transistors (OFETs) [9][10][11][12][13][14][15]. Taking

Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts

• Stefan Riedmüller and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2013, 9, 1202–1209, doi:10.3762/bjoc.9.136

• ., alkaloids) and pharmaceuticals [1]. In addition, the carbazole motif constitutes an immense class of materials in the rapidly growing field of molecular electronics. In particular N-arylcarbazoles have promising electroluminescent properties and have subsequently found diverse applications as hole-transport

• same reaction. Significantly lower yields were observed due to undesired side reactions involving benzyne intermediates by β-elimination. Representative examples of carbazoles with hole-transport, host or luminescent properties. FID chromatogram of the reaction mixture. Only the most intense peaks were

Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan

• Axel G. Griesbeck,
• Jörg Neudörfl and
• Alan de Kiff

Beilstein J. Org. Chem. 2011, 7, 518–524, doi:10.3762/bjoc.7.60

• herein, tryptophan is described in biological electron-transfer processes as the most active hole transport molecule [17]. Thus, it can be concluded that the excited charge-transfer state from 10, as can be interpreted from its fluorescence spectrum, is rapidly deactivated radiatively as well as non

New diarylmethanofullerene derivatives and their properties for organic thin- film solar cells

• Daisuke Sukeguchi,
• Surya Prakash Singh,
• Mamidi Ramesh Reddy,
• Hideyuki Yoshiyama,
• Rakesh A. Afre,
• Yasuhiko Hayashi,
• Hiroki Inukai,
• Tetsuo Soga,
• Shuichi Nakamura,
• Norio Shibata and
• Takeshi Toru

Beilstein J. Org. Chem. 2009, 5, No. 7, doi:10.3762/bjoc.5.7

• buffer layer for hole transport and reducing the roughness of the ITO surface, was spin-coated by 2000 rpm on the ITO-glass substrate with a thickness of ~80 nm from aqueous solution. The layer was then annealed at 120 °C for 10 min to remove the residual water. An ODCB solution of P3HT and the

• Ω/cm2) substrate was cleaned successively with acetone, methanol, and a copious amount of water, and dried by a N2 blower. The conducting polymer, poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS, Sigma-Aldrich), acting as a buffer layer for hole transport and reducing the