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

• endoperoxide formation. To overcome these issues, the “precursor approach” was developed and relies on the synthesis, purification and characterization of soluble and stable precursors of the target active π-CPCs, followed by their (solution) processing and their final deprotection once assembled in thin-films

• ” was next tested at the device fabrication stage in the case of OFETs. An Al2O3/SiO2 dielectric layer with a self-assembled monolayer of 12-cyclohexyldodecylphosphonic acid was chosen as substrate and thin-films of sulfoxide 4a were formed by spin-coating from a chloroform solution. After thermal

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

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

• . Photoelectrical and charge-transporting properties The ionization potentials (IPPE) of thin films were obtained by photoelectron emission (PE) spectroscopy in air (Figure 7 and Table 1). To generate photoelectrons detectable by a counter electrode within the PE experiments, a low-power deuterium UV lamp was used

• . It was previously shown that the PE technique gives practically the same IPPE values as they are recorded by other methods in vacuum [17]. The PE spectra as current (i) versus photon energy (hν) dependences for thin films of compounds 6–9 are built in the square root of i versus linear hν plots

• photoluminescence behavior of thin films, steady-state and time-resolved PL spectra were acquired using an Oxford Instruments Optistat DN2 cryostat, which was cooled with liquid nitrogen. The PL decay curves were obtained using a PicoQuant LDH-D-C-375 laser as the excitation source, operating at a wavelength of 374

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

• seen from Table 1, the kr of TPECNz in solution is larger than knr, which is consistent with the the observerd high PLQY in solution. On the other hand, knr of TPECNz in thin films is significantly higher than the knr of solution, explaining the drop of PLQY in thin films as compared to the PLQY in

• solution. However, the moderate PLQY in thin films still makes TPECNz suitable for the deep-red OLEDs. In addition, the AIE characteristic of TPECNz was further investigated by observing its PL emissions in water/THF mixtures with different water fractions (fw = 0–95%). In such diverse solvent mixtures

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

• the previously reported cyanated N-annulated perylene diimide (CN-PDIN-H), the N-position was functionalized with a benzyl and pentafluorobenzyl group to make CN-PDIN-B and CN-PDIN-FB, respectively. The materials exhibit solubility in the green solvent, ethyl acetate, and thus were processed into thin

• films using ethyl acetate as the solvent. The optoelectronic properties were assessed for both solution and film, and the electrochemical properties were probed in solution. To validate the potential as electron transporting layers, each film was used in conventional OPVs as the CIL with processing from

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

• DiKTa (λPL = 466 nm, FWHM = 40 nm, ΦPL = 70%, ΔEST = 0.20 eV, τD = 168 μs, 2 wt % mCP) in the same host [28]. Both emitters exhibited high ΦPL values in the mCP film at 71% and 61% under nitrogen, and these reduced to 57% and 53% in air for DiKTa-OBuIm and DiKTa-DPA-OBuIm, respectively. As neat thin

• films, the emission for both compounds are red-shifted and significantly quenched (Figure S28 in Supporting Information File 1); indeed, the ΦPL for the neat film of DiKTa-OBuIm is only 9% while we could not ascertain a reliable value for DiKTa-DPA-OBuIm. Severe aggregation-caused quenching of the

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

• Ashish Kumar Mazumdar,
• Gyana Prakash Nanda,
• Nisha Yadav,
• Upasana Deori,
• Upasha Acharyya,
• Bahadur Sk and
• Pachaiyappan Rajamalli

Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

• (d) BPy-p3C in toluene solution. Fluorescence intensity vs number of exposures for (a) BPy-p3C and (b) BPy-pTC thin films upon exposure to TFA and TEA vapors. Synthetic schemes of BPy-pTC and BPy-p3C. Photophysical properties of BPy-pTC and BPy-p3C.a Photophysical properties of BPy-pTC and BPy-p3C

Cs₂CO₃-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones

• Ol'ga G. Volostnykh,
• Olesya A. Shemyakina,
• Anton V. Stepanov and
• Igor' A. Ushakov

Beilstein J. Org. Chem. 2022, 18, 420–428, doi:10.3762/bjoc.18.44

• spectra were recorded on a Bruker DPX-400 spectrometer (400.1 and 100.6 MHz, respectively) in CDCl3 or (CD3)2CO using hexamethyldisiloxane as internal reference at 20–25 °C. IR spectra were measured on a Varian 3100 FT-IR Excalibur series instrument as thin films or KВr pellets. Microanalyses were

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

• absorption spectra of 69, 71, and 72 in chloroform displayed strong absorption at 667, 670, and 627 nm, and in the thin-film form they were further red-shifted. The optical energy gaps for 69, 71, and 72 were 1.33, 1.38, and 1.23 eV, respectively. Thin-films of 69 and 71, in which azulene was incorporated

• , respectively. The response to protonation (TFA) of these polymers was noteworthy as they exhibited rapid and reversible color changes both in solution and thin-film state. The direct current (DC) conductivity values recorded for the thin films of the protonated polymers 126 and 129 were 2.94 and 0.32 S/cm

• the percentage of azulene in the polymer backbone. The thin films of these polymers exhibited electrochromism, where the color changed from yellowish green (neutral and reduced state) to greyish brown (oxidized state) with electrochromic contrasts of 17 and 13% for polymers 137 and 138, respectively

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

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

• the morphology of thin films of the photovoltaic cells. To date, the maximum efficiency of 12.05% has been shown by an OSC based on a composite of a donor polythiophene and an acceptor polymeric dicyanoindanone derivative [13]. Among the derivatives of isoindigo, the leading compounds are polymers 1–3

• 60a,b are able to effectively bind gaseous ammonia molecules (Scheme 29) [106]. Thin films of these polymers are characterized by high sensitivity, reproducibility, and fast response time. Among this series of compounds, polymer 60b, containing a terthiophene oligomeric unit, has the best

• electron donor/acceptor nature, the heterocyclic substituents, and the branching of the alkyl radical at the endocyclic nitrogen atom. Research on methods to obtain polymer isoindigo thin films and the use of additives will, in our opinion, significantly improve the efficiency of materials. In addition

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

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

• solubility of the photocatalyst being poor in those solvents [139]. 2.4 Solid-supported semiconductors and metal nanoparticles For the same reasons outlined in the previous section, the immobilisation of thin films of semiconductors and the deposition of metal nanoparticle photocatalysts can improve the

• treatment [146]. Dip-coating has also been commonly applied to coat other inorganic substrates, such as glass spheres, carbon nanotubes, and diatomite with TiO2 thin films for photocatalysis applications [147][148][149][150]. Scaiano and co-workers deposited platinum nanoparticles on TiO2(P25) powder as a

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

• points of the compounds were determined with an Electrothermal MEL-TEMP apparatus. Absorption spectra of dilute solutions (10−4–10−5 mol/L) and thin films of the synthesized compounds were recorded with a Perkin Elmer Lambda 25 spectrophotometer. Fluorescence and phosphorescence spectra of thin films and

• dilute solutions (10−4–10−5 mol/L) of the compounds were recorded at room (295 K) and low (77 K) temperatures with a luminescence spectrometer Edinburgh Instruments FLS980. Photoluminescence quantum yields (PLQY) of the solutions and thin films of the materials were measured using an integrating sphere

• thin films of compounds 1–3 (λexc = 350 nm and PL decay curves (b) of thin films of derivatives 1–3 recorded at different emission wavelengths. Electron and hole NTOs of compounds 1–3 in the S1 excited state (vacuum). Chemical structures of exciplex-forming materials used, and visualization of white

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

• presence of a palladium catalyst, with yields ranging from 27 to 50%. The chemical structures of 3–6 were confirmed by 1H and 13C NMR spectroscopy, elemental analysis and mass spectrometry. Transparent thin films of these compounds could be prepared by vacuum evaporation or by spin coating from solutions

Probing of local polarity in poly(methyl methacrylate) with the charge transfer transition in Nile red

• Aydan Yadigarli,
• Qimeng Song,
• Sergey I. Druzhinin and
• Holger Schönherr

Beilstein J. Org. Chem. 2019, 15, 2552–2562, doi:10.3762/bjoc.15.248

• permittivity of polymers and its spatial distribution play a crucial role in the behavior of thin films, such as those used, e.g., as sensor coatings. In an attempt to develop a conclusive approach to determine these quantities, the polarity of the model polymer poly(methyl methacrylate) (PMMA) in 600 nm thin

• , respectively, were obtained for NR. An effective local dielectric constant of 5.9–8.3 for PMMA thin films was calculated from the solvatochromic plot and the fluorescence maximum of NR observed in the PMMA films. The fluorescence band of NR in the rigid PMMA films shifted to the red by 130 cm−1 with increasing

• polymers possess an enormous impact on the properties of polymers and polymer thin films. For ultrathin films, in which the film thickness is in the order of the radius of gyration, special effects of confinement have been observed. Prominent examples are the properties of substrate-supported ultrathin

Photochromic diarylethene ligands featuring 2-(imidazol-2-yl)pyridine coordination site and their iron(II) complexes

• Andrey G. Lvov,
• Max Mörtel,
• Anton V. Yadykov,
• Frank W. Heinemann,
• Valerii Z. Shirinian and
• Marat M. Khusniyarov

Beilstein J. Org. Chem. 2019, 15, 2428–2437, doi:10.3762/bjoc.15.235

• at the iron(II) ion at room temperature (rt) in solution via ligand photocyclization [19]. More recently, the remarkable photoswitching between high-spin and low-spin states at rt in the solid state and thin films was demonstrated [20][21][22]. Kawai et al. obtained a luminescent complex of europium

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• room temperature and the resulting polymers were processed as thin films. As a result of the dynamic nature of the Diels–Alder adducts, the films were shown to possess self-healing capabilities [190]. Similarly, Wei et al. employed DAC to create a self-healing hydrogel using a polysaccharide

Studies towards the synthesis of hyperireflexolide A

• G. Hari Mangeswara Rao

Beilstein J. Org. Chem. 2018, 14, 2106–2111, doi:10.3762/bjoc.14.185

• evaporator. Melting points were recorded on JSGW melting point apparatus and are uncorrected. Infrared spectra were recorded on Perkin-Elmer 1320 and Shimadzu 420 spectrophotometers as KBr pellets (solids), or as thin films on NaCl flats (liquids). 1H NMR spectra were recorded at 400 MHz on a JEOL

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

• Vladimir A. Burilov,
• Guzaliya A. Fatikhova,
• Mariya N. Dokuchaeva,
• Ramil I. Nugmanov,
• Diana A. Mironova,
• Pavel V. Dorovatovskii,
• Victor N. Khrustalev,
• Svetlana E. Solovieva and
• Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

• or DMSO-d6) as internal standard. MALDI mass spectra were measured on an UltraFlex III TOF/TOF with PNA matrix, laser Nd:YAG, λ = 355 nm. The IR spectra were recorded on a Bruker Vector-22 spectrometer. Samples were prepared as suspension in mineral oil or as thin films, obtained from chloroform

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

• supplementary interactions reinforced the ligand–metal bond, which explains well the remarkable phosphorescence efficiency obtained in solid-state thin films being PLQY of 0.52 and 0.83 for 8 and 9, respectively. Such findings prompted the authors to fabricate non-doped OLEDs with an architecture as follows

• alkynylplatinum(II) complexes with cyclometalated 2,6-bis(N-alkylbenzimidazol-2’-yl)benzene (bzimb) as the N^C^N tridentate ligand [62]. These complexes were found to be highly emissive with PLQYs of up to 0.80 in solid-state thin films. Contrarily to other alkynylplatinum(II) complexes, their emission was

• ascribed to an admixture of 3IL/3MLCT since no influence of the dendrimeric ancillary ligand was observed. Nevertheless, upon increasing the dopant concentration in thin films up to 50 wt %, a new low-energy band was observed that was attributed to the formation of excimeric species. Nonetheless, it is

Enhanced quantum yields by sterically demanding aryl-substituted β-diketonate ancillary ligands

• Rebecca Pittkowski and
• Thomas Strassner

Beilstein J. Org. Chem. 2018, 14, 664–671, doi:10.3762/bjoc.14.54

• complexes were measured on a Perkin Elmer lambda 25 spectrophotometer in dichloromethane solution. Photoluminescence measurements were performed in amorphous PMMA thin films doped with the emitter. Films were prepared by doctor blading a solution of 2 wt % emitter in a 10 wt % PMMA solution in

• , under N2. Thin films of Pt(MPIM)(acac) left, Pt(MPIM)(mes) (2) middle, and Pt(MPIM)(dur) (3) right, 2 wt % in PMMA under irradiation with ultraviolet light (365 nm). Photoluminescence spectra of 2 and 3 compared to the emission profile of Pt(MPIM)(acac), 2 wt % in PMMA, λexc = 320 nm. Localization of

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

Synthesis of naturally-derived macromolecules through simplified electrochemically mediated ATRP

• Paweł Chmielarz,
• Tomasz Pacześniak,
• Katarzyna Rydel-Ciszek,
• Izabela Zaborniak,
• Paulina Biedka and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2017, 13, 2466–2472, doi:10.3762/bjoc.13.243

• , and 1H NMR prove the successful preparation of the star-shaped polymers. These new polymer materials create potential possibilities of using them as key elements of biologically active thin films in tissue engineering and as drug delivery systems. 1H NMR analysis of QC-Br5 (Mn = 1,050, Ð = 1.11) after

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• , it is considered that the performance of solar cells that use per(trifluoroethoxy)phthalocyanine, which exhibits a strong repulsion effect, will be low. It is expected that phthalocyanine will be put to practical use within solar cells by improving the orientation control in thin films. Development