Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• crystals (F-DLCs) [13][14][15][16][17] of interest for organic electronics and optical advanced materials, as they tend to promote more efficient molecular stacking into columns than their purely hydrogenated counterparts [18][19], thereby improving one-dimensional charge transport properties [20][21][22

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

• leads to the formation of large crystalline domains which influence charge transport. However, the microscale domains reduce the donor–acceptor interface which ultimately impacts on efficient exciton dissociation in OPV devices [12]. Therefore, it is important to further investigate other fused π

• structural features of violanthrones suggest that these materials may possess similar charge transport, optical and electrochemical properties to those of PDIs. However, the larger π-conjugated system of violanthrone, along with the two carbonyl groups, increases the possibility of stronger π–π

• potentially efficient and isotropic charge transport [12]. It is also evident that the presence of the two dicyanomethylene groups in compound 3 are responsible for lowering the energy of the two frontier molecular orbitals and for narrowing the energy gap between HOMO and LUMO. This is likely due to an

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

• molecular ordering in solid-state organic semiconductors, thereby dictating charge transport pathways as well as carrier mobilities of both electrons and holes [4][5][6]. Furthermore, strong hydrogen bonding interactions effectively modulate energy levels of semiconducting materials, affecting the bandgap

• perylenebisimide (PBI) components connected laterally through H-bonding and self-assembled orthogonally through π–π interactions [13]. Mixtures of PBI and OPV successfully exhibited ambipolar charge transport depending on processing conditions as a result of the co-assembled morphology. Our group utilized a

• derivative 2b further revealed that it adopts a favorable herringbone motif characterized by short π–π distances and extensive intermolecular hydrogen bonding. These structural features are anticipated to promote efficient charge transport. Future work will involve device fabrication and comparison of the

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

• same protocol with a photoconversion of 4a thin-film instead of thermal conversion, a decrease of the charge transport efficiency was observed, with electron mobilities of 8.4 × 10−2 cm2 V−1 s−1, which can be ascribed to the lower quality of the PBI thin-film generated upon photoextrusion due to the

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• stability, showing no signs of degradation over an extended period when kept in the dark, both in solid form and in solution under air. In the final phase of the study, the authors investigated the charge-transport properties of compond 34a in OFET. Since the charge-transport properties are significantly

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

• compounds. In general, polyaromatic π-systems with pyridine-3,5-dicarbonitrile fragments demonstrate promising potential for use in organic electronic devices, such as OLEDs. Keywords: charge transport; intramolecular charge transfer; photophysical properties; pyridine-3,5-dicarbonitrile; Introduction The

• with pyridine-3,5-dicarbonitrile fragments demonstrated a range of attractive properties, including efficient TADF, favorable charge transport, and thermal stability. These findings open up new possibilities for the design and development of high-performance OLEDs and other organic electronic devices

• compounds. To accurately assess the hole and electron mobility in vacuum-deposited layers of the investigated compounds, we employed the time-of-flight (TOF) method, a reliable technique for characterizing charge transport in organic materials. Our TOF experiments involved samples with a structured

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

• understanding charge transport in columnar mesophases [9][10][11][12][13][14]. High charge carrier mobilities of 1.1 cm2 V−1 s−1 for p-type and up to 6.0 cm2 V−1 s−1 for n-type liquid-crystalline semiconductors have already been reported [15]. Among the various discotic liquid crystal materials, perylene

• charge transport behavior. DFT calculations assisted the interpretation of electron and hole migration mechanism using the frontier orbital energies and the conjugation within the π-system. Results and Discussion The syntheses of 1 and 2 were previously published in [25] and [26], respectively. 1 is a

• literature [24]. It is important to emphasize that the charge carrier mobility of columnar liquid crystals can be improved by five orders of magnitude due to molecular alignment of the film in the device structure [33]. Usually, the π-system conjugation and the frontier orbitals energies dominates the charge

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

• 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

• emerged as a promising class of heterocyclic compounds for charge transport applications, owing to two crucial factors. Firstly, their structural diversity enables precise customization of molecular structures, allowing for fine-tuning of their properties and optimization of performance for specific

• 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

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

• charge-transport properties, which could be done by selecting different D and A moieties [22][26][27][28]. In these fluorophores, the emission generally derives from intramolecular charge-transfer (CT) states at lower energy. Nonetheless, the formed CT state between D and A in such materials normally

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

• investigation of the processes involved in the formation of the interfacial layer between the donor–acceptor and the charge transport layer. Nevertheless, based on all the optoelectrical characterization, proposed N-annulated perylene diimides-based CILs are suitable candidates for CILs that can be replaced

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• fluorescence; Introduction Light-emitting electrochemical cells (LEECs) are thin film light-emitting devices typically consisting of an emissive layer containing ionic species that facilitate charge transport and an emissive semiconductor material. The emissive layer is sandwiched between two air-stable

Electrochemical and spectroscopic properties of twisted dibenzo[g,p]chrysene derivatives

• Tomoya Imai,
• Ryuhei Akasaka,
• Naruhiro Yoshida,
• Toru Amaya and
• Tetsuo Iwasawa

Beilstein J. Org. Chem. 2022, 18, 963–971, doi:10.3762/bjoc.18.96

• , dyes, liquid crystals, and light-emitting materials. A number of substituted DBCs have been reported in this context [27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46]. To develop charge-transport materials, Rathore et al. reported on the stability of radical cations of

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

• a certain application, for example where charge transport is more important than photoluminescence quantum yield or vice versa. Introducing alkyl chains can provide solubility, enabling facile solution processing, such as device printing techniques [13]. Hence, there is an ongoing interest in

• -conjugated ring structures [15]. In the solid state, fused systems are prone to form highly ordered π–π-stacked structures [16], leading to better bulk charge transport [17]. Another important aspect is solubility, which is generally poor in larger conjugated molecules [3]. This is even aggravated for fused

Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

• Mengjie Wang,
• Lanping Dang,
• Wan Xu,
• Zhiying Ma,
• Liuliu Shao,
• Guangxia Wang,
• Chunli Li and
• Hua Wang

Beilstein J. Org. Chem. 2022, 18, 809–817, doi:10.3762/bjoc.18.81

• annulene [12], and twisted naphthalene as central spacers [19]. As its close analogue, selenophene has properties very similar to those of thiophene. Fused aromatic compounds containing selenophene units show favorable optical and electrochemical properties and improved charge transport characteristics in

• the solid state mainly because such fused aromatic compounds often undergo increased Se–Se interactions, which confer ordering at the molecular scale and, thus, lead to well-aligned solid-state packing and excellent charge-transport properties [20][21]. However, as an important type of heteroacenes

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• potential applications ranging from the chemistry perspective to materials science and technology [1][2][3][4]. As we know that bowled (curved) surfaces are universal in nature for example our planets as well as atomic orbitals possess the curvature which generally affects the charge-transport, redox, self

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

• , brookite, and rutile (Figure 3A). The different lattice structures influence the atomic orbital environments and energy, which alters the photophysical and charge transport properties of the material, which has been studied in great detail [78][79][80][81][82]. The titanium and oxygen atomic orbitals

• polymer chains, charge transport is limited to intraplanar transport along the conjugated network. In crystalline and graphitic organic materials, the close packing of two-dimensional sheets permits interplanar charge transport in the third dimension, allowing the delocalisation of charge over several

• molecular layers [107]. The complex models used to describe charge transport in organic materials with differing degrees of disorder is well described by Liu, Noh, and co-workers [108]. The relative permittivity or dielectric constant (εr(ω)), which influences the screening of the charge carriers within the

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

• Rasa Keruckiene,
• Simona Vekteryte,
• Ervinas Urbonas,
• Matas Guzauskas,
• Eigirdas Skuodis,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

• ; quinazoline; Introduction Organic luminescent materials are extensively used in a wide range of optoelectronic devices. For the design of compounds, potentially exhibiting properties such as bipolar charge transport, delayed fluorescence or aggregation-induced emission enhancement (AIEE), a useful strategy

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

• much more emissive than compound 7a, in which the formyl group is at the meta position to the carbazole ring. Conclusion In this work, two novel compounds 7a and 7b were successfully synthesised in good yields and demonstrated good thermal stability. Compounds 7a and 7b showed intramolecular charge

• transport properties with positive solvatochromism. Whilst 7a showed very low emission intensity, 7b showed very high emission intensity. It is noted that the conjugation in compound 7b encompasses the N atom of the carbazole ring and the formyl functionality (viz. the donor/acceptor units of the ICT

Aryl-substituted acridanes as hosts for TADF-based OLEDs

• Naveen Masimukku,
• Dalius Gudeika,
• Oleksandr Bezvikonnyi,
• Ihor Syvorotka,
• Rasa Keruckiene,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 989–1000, doi:10.3762/bjoc.16.88

• applied in TADF-based OLEDs so far [20][21]. Although these hosts demonstrate relatively good results, it can be presumed that the further improvement of the performance of TADF-based OLEDs is possible, if some drawbacks of widely used hosts such as unipolar charge transport or uncomplimentary energy

• interaction. Charge transporting properties To unclose the potential of acridan-based derivatives containing phenyl or naphthyl substituents as hosts for blue TADF OLEDs, charge-transport properties of the vacuum deposited layers of the acridanes were tested by the methods of time-of-flight (TOF) and charge

• CELIV method, which is less sensitive to charge-transport dispersity than the TOF method, was additionally exploited for charge-transport characterization of the compounds. Indeed, well discernible maxima were observed not only for the layers of compound 4 but also for the layers of 5 and 6 (Figure 5c,d

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• molecules containing selenophene fragments instead of thiophene showed promising optical and electrochemical properties [17][18][19] and improved charge transport characteristics [20]. With respect to fused selenoloacenes, only the shortest parent system consisting of two fused heterocycles, mixed thieno

Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium

• Xin Shen,
• Bo Li,
• Tiezheng Pan,
• Jianfeng Wu,
• Yangxin Wang,
• Jie Shang,
• Yan Ge,
• Lin Jin and
• Zhenhui Qi

Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117

• properties, such as charge transport and photophysical properties [69][70][71][72][73][74]. While the morphologies of these aggregates were greatly influenced by solvents, molecular structures and shapes, as well as the fraction of hydrophilic and/or hydrophobic parts [75][76][77][78][79][80][81]. By far

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

• Cristina Cebrián and
• Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

• affect the final performances [60]. Alternatively, development of emissive complex incorporated in a dendritic structure allows controlling both charge transport and light emission in a single material [61]. In this regard, Yam and co-workers reported on a series of dendritic carbazole-based

• )-9,9′-spirobifluorene. For all devices, emission similar to those recorded in solution was obtained independently of the doping concentration. Moreover, the decreasing driving voltages measured were ascribed to better charge transport properties in the emissive layer upon increasing the dendron

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

• , but EL polymers substituted with iridium complexes have previously been studied in the literature, evidencing the pertinence of the strategy [61]. In this case, charge transport properties are provided by the substituents attached to the polymer chain. As main finding of this work, the detrimental

• Figure 11) [69]. The choice of pyridine-3,5-dicarbonitrile as acceptor was notably motivated by the outstanding charge-transport ability and the remarkable electrochemical stability of this group [70][71]. Thus, CN-P1 had a small singlet−triplet splitting (ΔEST = 0.04 eV), fairish PLQY in doped films

• reducing the global energy demand on Earth, two parameters govern the power consumption of OLEDs, namely the quantum yield of luminescence of the light emitting material and the device stacking. Indeed, the driving voltage of OLEDs is highly sensitive to the thickness of the different layers, the charge

Comparing blends and blocks: Synthesis of partially fluorinated diblock polythiophene copolymers to investigate the thermal stability of optical and morphological properties

• Pierre Boufflet,
• Sebastian Wood,
• Jessica Wade,
• Zhuping Fei,
• Ji-Seon Kim and
• Martin Heeney

Beilstein J. Org. Chem. 2016, 12, 2150–2163, doi:10.3762/bjoc.12.205

• thin-film microstructure playing such a key role in the optoelectronic and charge transport properties of conjugated polymers, block copolymers naturally appear as useful tools for tailoring the thin-film morphology [1][2][3][4][5]. The propensity of some block copolymers to phase segregate at the nano

Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

• Desta Gedefaw,
• Marta Tessarolo,
• Margherita Bolognesi,
• Mario Prosa,
• Renee Kroon,
• Wenliu Zhuang,
• Patrik Henriksson,
• Kim Bini,
• Ergang Wang,
• Michele Muccini,
• Mirko Seri and
• Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

• to have sufficient solubility in common organic solvents, good stability in air, a suitable bandgap for an effective light harvesting, proper charge transport properties, suitable HOMO and LUMO energy levels compatible with the acceptor material [13] and an excellent film-forming capability. In

• , which simultaneously increase from PTzBDT-1 to PTzBDT-2, are the main parameters responsible for the different photovoltaic responses. Interestingly, the FF is identical for both films (64%), indicating suitable charge transport properties within the blends. By comparing the VOC values an increase of