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

• annealing at 230 °C for 5 min to induce SO-extrusion and subsequent vacuum deposition of the source and drain gold electrodes, the resulting OFET exhibited a typical n-type behavior with an electron mobility up to 0.41 cm2 V−1 s−1, comparable to vacuum deposited films of pristine PBI. When repeating 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

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, offering a range of properties specifically tailored for OFET applications. The tunable properties of Qxs as n-type semiconductor materials, including high electron mobility, optimal energy levels, broad absorption spectra, and processing compatibility, position them as promising candidates for

• exhibited low LUMO levels and two-dimensional carrier transport, enabling OFET performance. The moderate air-stable n-channel mobility of 0.044 cm2 V−1 s−1 demonstrated the suitability of these derivatives for electron transport [52]. Hayashi et al. introduced a new avenue for developing n-type N

• section "Quinoxalines as polymer acceptors" also fabricated OFETs using QxCN-based polymer acceptors and demonstrated unipolar n-type characteristics with moderate OFET mobilities. The well-ordered structures with tight π–π stacking in Qx2 and Qx3 contributed to electron mobilities greater than 1.0 × 10−4

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

• s−1. Keywords: dithienothiophene (DTT); fused ring system; organic field-effect transistor (OFET); organic semiconductor; thienoacene; Introduction In recent years, organic molecules with several fused aromatic rings have gained much attention. Fusing aromatic rings leads to planar structures

• . EtH-T-DI-DTT (1). Previously published, ‘bent’ diindenodithienothiophenes [16][24][25]. With crystalline films of 2,7-dioctyl[1]benzothieno[3,2-b][1]-benzothiophene (8), obtained by off-centre spin-coating, Bao et al. could obtain remarkable OFET hole mobilities of up to 43 cm2 V−1 s−1 [27]. An

• asymmetric analogue, which is only alkylated on one side (9), achieved OFET hole mobilities up to 17.22 cm2 V−1 s−1 in polycrystalline films obtained by thermal evaporation [28]; both examples prove the potential of thienoacenes in OFETs. ITIC, a system with fused thiophenes, in combination with donor

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

• for 81 and 0.24 cm2 V−1 s−1 for 83. The polymer 81 with an electron mobility of 0.42 cm2 V−1 s−1 represents one of the best unipolar n-type polymers for OFET applications. These polymers were also tested as electron acceptors for all-polymer solar cell (PSC) devices, and 81 in particular, showed a

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

• [11][12], the 2,2’-bianthracene derivative 3 provides a green and fluorescent OLED [13], 2,2’-bianthracenyl (4) has been employed as an organic semiconductor in an OFET device [14], and di-n-alkoxyanthracenes have gelling properties with diverse solvents, mainly alkanes and alcohols [4]. Furthermore

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

• of functional materials are analyzed and summarized. These bisheterocycles can be used in the creation of organic solar cells, sensors, lithium ion batteries as well as in OFET and OLED technologies. The potentials of the use of polymer structures based on isoindigo as photoactive component in the

• 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

• 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

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

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

• the optical and electrochemical measurements and OFET performances, respectively. Finally, they were applied as the hole-transporting layer of the PSCs, and the photovoltaic properties of both devices were compared. The device based on 2,7-Cbz-EDOT displayed a higher PCE of 4.47% than that based on

• properties of the Cbz-EDOT polymers, top-contact/bottom-gate type OFET devices were fabricated, and the transistor performances were initially evaluated in air (for details see Supporting Information File 1). Both Cbz-EDOT polymers showed a p-type unipolar behavior during the measurements (Figure S2

• polycondensation. Optical, electrochemical, and electrical properties of Cbz-EDOT polymersa. Photovoltaic parameters of PSCs based on 3,6-Cbz-EDOT, 2,7-Cbz-EDOT, and P3HT. Supporting Information Supporting Information File 210: Synthesis of carbazole derivatives, 1H NMR and IR spectra of the polymers, and OFET

Syntheses of dibenzo[d,d']benzo[2,1-b:3,4-b']difuran derivatives and their application to organic field-effect transistors

• Minh Anh Truong and
• Koji Nakano

Beilstein J. Org. Chem. 2016, 12, 805–812, doi:10.3762/bjoc.12.79

• has been reported to demonstrate an excellent OFET mobility of 3.6 cm2·V−1·s−1 [19]. Previously, we have reported the synthesis of dibenzo[d,d']benzo[1,2-b:4,5-b']difurans (anti-DBBDFs), which is also a π-extended homologue of BDF [35]. The OFET devices with an anti-DBBDF skeleton exhibited p-type

• . The highest hole mobility of 1.0 × 10−1 cm2·V−1·s−1 was achieved when using syn-DNBDF-based OFET device. Structures of furan-fused ladder-type π-conjugated compounds. (a) DSC and (b) TG curves of syn-DBBDF 5 and syn-DNBDF 6. (a) UV–vis absorption spectra of syn-DBBDF 5 (blue line) and syn-DNBDF 6 (red

• Information File 96: General experimental procedures, synthetic procedures/characterization data of compounds 5–12, device fabrication/evaluation procedures, OFET characteristics, XRD patterns, and AFM images. Acknowledgements This work was partially supported by MEXT KAKENHI Grant Number 26104510. A part of

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• formation of TTF cation radical and dication were not apparent in the CV of the film, but were discernible in solution state. Pure 13e, and 13e with a small amount of the parent poly(3,3'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene) (PQT12) (5 or 10 wt %), did not exhibit any OFET activity due to hole

• trapping by the TTF unit. This hole trapping was explained to be the reason for a negative Seebeck coefficient of the non-doped polymer 13e and was used for sensing trinitrotoluene (TNT) using the drain-source current-increase response to TTF-TNT complexation in an OFET fabricated from 13e with 5% of PQT12

• from those in solution (−4.95/−3.55 eV), which suggested significant donor–acceptor interactions in the solid phase between the DPP and TTF units. OFET device fabrication employing polymer 48 exhibited p-type semiconductor behaviour, with the best performance from devices using the bottom contact top

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

• Rupert G. D. Taylor,
• Joseph Cameron,
• Iain A. Wright,
• Neil Thomson,
• Olena Avramchenko,
• Alexander L. Kanibolotsky,
• Anto R. Inigo,
• Tell Tuttle and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

• and electrochemical properties of compounds 1 and 2 have been measured by UV–vis spectroscopy and cyclic voltammetry and the results compared with density functional theory (DFT) calculations to confirm the observed properties. Organic field effect transistor (OFET) devices fabricated from 1 and 2

• interactions; organic field effect transistor (OFET); organic semiconductors; tetrathiafulvalene; thiazole; Introduction The TTF moiety has received much attention in the field of organic electronics owing to its reliable redox behaviour [1], good charge transport properties [2] and scope for

• suggests that the improvement in OFET performance with the addition of PFBT is due to improved charge injection, rather than an improvement in the morphology of the film. The OFETs were tested for n-type mobility but there was no field-effect observed. Interestingly, despite OFETs fabricated from compound

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

• Bradley D. Rose,
• Peter J. Santa Maria,
• Aaron G. Fix,
• Chris L. Vonnegut,
• Lev N. Zakharov,
• Sean R. Parkin and
• Michael M. Haley

Beilstein J. Org. Chem. 2014, 10, 2122–2130, doi:10.3762/bjoc.10.219

• heteroatoms, etc.) [1][2][3]. Recently there has been resurging interest in PCHs for use as active materials in organic electronic devices. Some popular examples of devices undergoing extensive exploration are organic field effect transistors (OFET) [4][5], organic photovoltaics (OPV) [6], and organic light

• anions [12]. The result of the IFs high electron affinity is nearly balanced ambipolar charge transport in OFETs [11][13]. The synthetic precursors to 1, the indeno[1,2-b]fluorene-6,12-diones (IF-diones, 2, Figure 1) have also been explored as an active layer in OFETs. The first reported IF-dione OFET

• utilized 3 – while the solid-state structure of 3 showed several sub-van der Waals contact distances, the n-type mobility of the OFET was very low (2 × 10−5 cm2 V−1 s−1) [14]. On the other hand, an OFET utilizing 4 (X = F) had measured electron mobilities of 0.17 cm2 V−1 s−1, and its X-ray crystal

Crystal design using multipolar electrostatic interactions: A concept study for organic electronics

• Peer Kirsch,
• Qiong Tong and
• Harald Untenecker

Beilstein J. Org. Chem. 2013, 9, 2367–2373, doi:10.3762/bjoc.9.272

• found practical application in printed circuits for driving e-paper displays [1][2]. Among the most critical parameters for their application in organic field effect transistors (OFET) are their charge carrier mobility and their solubility in non-toxic organic solvents for processing by printing

The efficient synthesis of dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene and cyclopenta[1,2-b:4,3-b′]bis(benzo[d]thiophen)-6-one

• Zhihua Wang,
• Sheng Zhu,
• Jianwu Shi and
• Hua Wang

Beilstein J. Org. Chem. 2009, 5, No. 55, doi:10.3762/bjoc.5.55

• ], have been developed and tested as active semiconducting channels in OFET devices due to their structural resemblance to pentacene [14] which possesses very high field-effect mobility (~3.0 cm2 V−1 s−1) for OFET devices. However, one of the possible analogs, dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene

• ][11][24][25]. Because of higher π-electron delocalization, compounds 1 and 2 could be used in OFET and/or conducting polymers. From 3 as starting material, 1 and 2 have been efficiently obtained in a total yield of 60% and 79%, respectively, in our work. The efficient synthesis of 1 and 2 will