Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

• Ettore Crovini,
• Zhen Zhang,
• Yu Kusakabe,
• Yongxia Ren,
• Yoshimasa Wada,
• Bilal A. Naqvi,
• Prakhar Sahay,
• Tomas Matulaitis,
• Stefan Diesing,
• Ifor D. W. Samuel,
• Wolfgang Brütting,
• Katsuaki Suzuki,
• Hironori Kaji,
• Stefan Bräse and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197

• eV for DICzTRZ vs −1.75 eV for ICzTRZ) since the electronic environment surrounding the t-Bu-triazine remains essentially unperturbed (Figure 3). Optoelectronic properties The electrochemical properties of the two materials were studied in degassed DCM with tetra-n-butylammonium hexafluorophosphate

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 2450–2461, doi:10.3762/bjoc.17.162

• and their optical and electrochemical properties investigation by the use of UV–vis and emission spectroscopy, CV measurements as well as DFT calculations. Results and Discussion Synthesis. At the beginning of this study, we synthesized 2,4-dibromo-9-chloro-5,6,7,8-tetrahydroacridine (2) by refluxing

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli,
• Noureddine Chaaben,
• Kamel Alimi,
• Stefan Jopp and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

• several types of tumors [21][22][23][24][25][26][27][28][29][30][31]. In recent years, much attention has been devoted to acridines in materials science due to their attractive photophysical and electrochemical properties [32][33][34][35]. They have been investigated in organic electronic devices [36][37

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

• °C (Scheme 7). A study of photophysical and electrochemical properties of compounds 3 is in progress and will be published elsewhere. Conclusion A wide range of derivatives with new pyrido[2,1-a]pyrrolo[3,4-c]isoquinoline skeleton was synthesized by free-radical intramolecular cyclization of o

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

• Mio Matsumura,
• Takahiro Teramoto,
• Masato Kawakubo,
• Masatoshi Kawahata,
• Yuki Murata,
• Kentaro Yamaguchi,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2021, 17, 671–677, doi:10.3762/bjoc.17.56

• –426 nm (Table 2). P-methylated cation 5 exhibited the longest wavelength and the highest quantum yield. The electrochemical properties of benzonaphthophosphoindoles were investigated by using cyclic voltammetry, and the electrochemical data are summarized in Table 3 and Figure S4, Supporting

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• % yield [100]. Photolysis of derivatives of para-substituted 3-fluoromethyl-3-phenyldiazirones in the presence of C60 gave phenylmethanofullerenes 53–56 in acceptable yields (Scheme 17) [101]. The electrochemical properties of the products were characterized by cyclic voltammetry and differential pulse

• (Scheme 33). Сoordination of these compounds with ruthenium(II) leads to a donor–bridge–acceptor assembly of complexes with various lengths, 187–189. It is believed [153] that the photophysical and electrochemical properties of the complexes presented are promising for the formation of charge-separated

Thermodynamic and electrochemical study of tailor-made crown ethers for redox-switchable (pseudo)rotaxanes

• Henrik Hupatz,
• Marius Gaedke,
• Hendrik V. Schröder,
• Julia Beerhues,
• Arto Valkonen,
• Fabian Klautzsch,
• Sebastian Müller,
• Felix Witte,
• Kari Rissanen,
• Biprajit Sarkar and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2020, 16, 2576–2588, doi:10.3762/bjoc.16.209

• corresponding free macrocycle. The detailed understanding of the thermodynamic and electrochemical properties of the tailor-made crown ethers lays the foundation for the construction of new types of molecular redox switches with emergent properties. Keywords: crown ether; isothermal titration calorimetry

• motivated us to conduct the present study on the thermodynamic and electrochemical properties of seven redox-active crown ethers of different ring sizes in comparison to the unfunctionalized analogs DBC8 and BC7 (Figure 1). Crown ethers incorporating TTF, an extended TTF, and naphthalene diimide (NDI) as

• . Results and Discussion Design considerations The nine crown ether wheels and two ammonium axles used in this study are depicted in Figure 1. Previously, we investigated the thermodynamic and electrochemical properties of pseudorotaxanes made from TTFC8 and exTTFC8 in two separate studies [35][37]. Herein

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

• ]rotaxane is a homologue of the versatile benchmark tetraamide variant developed by Leigh and co-workers. The relative templating effect of different hydrogen-bonding motifs in rotaxane and pseudorotaxane generation is compared, with yields varying from 0 to 41%. The electrochemical properties and single

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

• [15]. Theoretical calculations and electrochemical properties DFT calculations were employed to gain insight into the structure–property relationships of the quinazoline-based derivatives 1–3. The compounds have phenyl spacers between the donor and acceptor units (Figure 2). Therefore, the dihedral

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

• of compounds 7a and 7b are depicted in Figure 1. Thermal properties of compounds 7a and 7b are also summarised in Table 1. Electrochemical properties The redox behaviour of compounds 7a and 7b was investigated by cyclic voltammetry in dichloromethane solution under argon atmosphere using

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

• values were estimated as 2.54 eV for 4, and 2.67 eV for 3 and 6. The triplet energy could not be estimated for derivative 5, since the phosphorescence at 77 K was practically undetectable for this compound. Electrochemical and photoelectrical properties The electrochemical properties of the acridane

• appropriate for an application as hole-transporting materials in organic optoelectronic devices. Conclusion Four new aryl-substituted derivatives of acridan were designed and synthesized as electroactive materials for organic light emitting diodes. The thermal, photophysical, and electrochemical properties of

• conditions: (a) bromoethane, KOH, tetrabutylammonium bromide, acetone, 60 °C, 1 h; (b) napthalen-1-ylboronic acid, 4-vinylphenylboronic acid or 4-fluorophenylboronic acid, K2CO3, PdCl2(PPh3)2, THF/H2O, 80 °C, 24 h. Thermal characteristics of acridan-based compounds 3–6. Electrochemical properties of compound

Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes

• Aya Yoshimura,
• Hitoshi Kimura,
• Kohei Kagawa,
• Mayuka Yoshioka,
• Toshiki Itou,
• Dhananjayan Vasu,
• Takashi Shirahata,
• Hideki Yorimitsu and
• Yohji Misaki

Beilstein J. Org. Chem. 2020, 16, 974–981, doi:10.3762/bjoc.16.86

• systems; electrochemical properties; extended π-conjugation; digital simulation analysis; tetrathiafulvalene; Introduction Tetrathiafulvalenes (TTFs) with extended π-conjugation have attracted attention as possible components of functional materials, such as molecular conductors, field-effect transistors

• direct C–H arylation was reported, and the structural and electrochemical properties of the products were clarified [30]. This motivated us to synthesize novel multistage redox-TTFs bearing 1,3-dithiole rings on aromatic rings, 1–3 (Figure 1). In addition, we focused on cross-conjugated systems with 1,3

• ), such as 4 (Figure 1), and the electrochemical properties of these representatives should be brought to light. Herein, we report the synthesis and electrochemical properties of tetrathiafulvalene derivatives 1–4. Results and Discussion Synthesis First, we tried to synthesize compounds 1 and 2 in one

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• conjugated photosensitizers show increasing potential in photocatalysis since they combine both photo- and electrochemical properties which can substitute available metalloorganic photocatalysts. Batch and continuous-flow approaches are presented highlighting the relevance of enabling technologies for the

One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation

• Ji Ma,
• Yubin Fu,
• Junzhi Liu and
• Xinliang Feng

Beilstein J. Org. Chem. 2020, 16, 791–797, doi:10.3762/bjoc.16.72

• 1.78 eV from the onset of its UV–vis absorption spectrum. Similar to the cyclopenta-fused pyrene derivatives [28][29], compound 1 does not show detectable fluorescence emission. Furthermore, the electrochemical properties of 1 was probed by cyclic voltammetry (CV) in DCM (Figure 3b). According to the

Towards triptycene functionalization and triptycene-linked porphyrin arrays

• Gemma M. Locke,
• Keith J. Flanagan and
• Mathias O. Senge

Beilstein J. Org. Chem. 2020, 16, 763–777, doi:10.3762/bjoc.16.70

• and electrochemical properties of the porphyrins by increasing the size of the aromatic π-system [16]. In contrast, our approach described herein deviates significantly from previous studies by examining how isolating the individual porphyrin units affects the overall photophysical properties of the

Synthesis of C₇₀-fragment buckybowls bearing alkoxy substituents

• Yumi Yakiyama,
• Shota Hishikawa and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2020, 16, 681–690, doi:10.3762/bjoc.16.66

• that with C60 fragment because most of them consists of acene and/or pyrene units, which might give unique photochemical and electrochemical properties. Recently, we synthesized a buckybowl C28H14 1, which is corresponding to a 40% fragment of C70, from C60-fragment sumanene (2) in three steps via ring

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties

• Takahide Shimada,
• Shigeki Mori,
• Masatoshi Ishida and
• Hiroyuki Furuta

Beilstein J. Org. Chem. 2020, 16, 587–595, doi:10.3762/bjoc.16.53

• substituted BODIPY cores, higher emission quantum yields of 0.86 and 0.77 were estimated, respectively (Table 1). Electrochemical properties Cyclic voltammetry and differential pulse voltammetry of the BODIPY derivatives 3a–6a were performed in dichloromethane solutions containing 0.1 M tetra-n-butylammonium

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

• Bernd Strehmel,
• Christian Schmitz,
• Ceren Kütahya,
• Yulian Pang,
• Anke Drewitz and
• Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

• properties and to tailor made the ΔGet photopysical properties with respect to absorption and fluorescence. Electrochemical properties were additionally considered for some selected examples. The cyanines chosen comprised as end groups either indolenine, benzo[e]- or benzo[cd]indolium pattern, which

• in changes of absorption maxima and electrochemical potentials appearing sometimes with rather low quantities, see Table 1 for explanation of the absorbers and Table 2 for the data vide infra. These synthetic efforts resulted in many distinct absorbers whose absorption and electrochemical properties

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

• Daniel R. Sutherland,
• Nidhi Sharma,
• Georgina M. Rosair,
• Ifor D. W. Samuel,
• Ai-Lan Lee and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2019, 15, 2914–2921, doi:10.3762/bjoc.15.285

• enhanced overlap of the HOMO and LUMO wave functions. Electrochemical properties The electrochemical behavior of 2–5 was studied by cyclic voltammetry and differential pulse voltammetry in degassed DCM with tetrabutylammonium hexafluorophosphate as the supporting electrolyte. The cyclic voltammograms (CVs

• monofunctionalization of BQ (1). Synthesis of 5 via double Suzuki coupling. Electrochemical properties of 2–5. Optoelectronic properties of 2–5. Supporting Information The research data supporting this publication can be accessed at https://doi.org/10.17630/178f3a7c-4717-43f0-a145-049675825e1a. Supporting Information

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• between anions and the NDI motif [59]. NDI was chosen due to its excellent photochemical and electrochemical properties. In addition, the electron deficiency and aromatic nature of NDI is important for anion–π interactions [60] to control the charge-transfer properties. It also has been observed that in

Naphthalene diimides with improved solubility for visible light photoredox catalysis

• Barbara Reiß and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 2043–2051, doi:10.3762/bjoc.15.201

• strength of chemical redox agents [60], cNDI 2 in the excited state is a strong oxidant and a mild reductant. We assume based on literature-known cNDIs that the different alkyl groups of the other cNDIs 3–6 have no or only very little influence on the electrochemical properties in comparison with those of

• effect cannot be excluded. Taken together, it makes clear that tuning of optical and electrochemical properties of potential photoredox catalysts have to be combined with their elucidation of their photophysical dynamic behavior. Conclusion The cNDIs 2–6 were synthesized as potential photoredox catalysts

• . The substrate conversion and product yields were significantly higher by LED irradiation into the absorbance shoulder at 520 nm which implies a non-Kasha-type photodynamic behavior. This makes clear that future photoredox catalysts must not only by tuned by their optical and electrochemical properties

Synthesis, photophysical and electrochemical properties of pyridine, pyrazine and triazine-based (D–π–)₂A fluorescent dyes

• Keiichi Imato,
• Toshiaki Enoki,
• Koji Uenaka and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2019, 15, 1712–1721, doi:10.3762/bjoc.15.167

• moiety, and the lowest unoccupied molecular orbital (LUMO) is localized over the A moiety. Thus, the photophysical and electrochemical properties based on the ICT characteristics of D–π–A dyes should be tuneable by not only the electron-donating ability of D and the electron-accepting ability of A, but

• ][18][19][20][21][22][23][24], and a promising photosensitizer for dye-sensitized solar cells (DSSCs) [25][26][27][28][29][30][31][32][33][34]. Thus, in this work, to gain insight into the photophysical and electrochemical properties of D–π–A fluorescent dyes with an azine ring as electron-withdrawing

• dyes OUY-2 [2] and OUK-2 [3][4] and their partial photopysical and electrochemical properties. One advantage of (D–π–)2A fluorescent dyes over other D–π–A fluorescent dyes is their broad and intense photoabsorption spectral features. Herein, based on photoabsorption and fluorescence spectroscopy

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

• 3/DSS 4 (28,400 to 20,830 L mol−1 cm−1). No fluorescence was observed for each of the four heteroacenes DTT 1 to DSS 4 neither in DCM nor in THF. Electrochemical properties and electropolymerization The redox properties of the heterotriacenes 1–4 were investigated by means of cyclic voltammetry in

• –P4 is slightly more negative compared to the non-bridged counterparts, namely poly(bithiophene) [48][49][50] and poly(biselenophene) [51] (both show Eonset at ca. −0.0 V vs Fc/Fc+) indicating that the chalcogenide bridges do not much influence the electrochemical properties of the corresponding

N-Arylphenothiazines as strong donors for photoredox catalysis – pushing the frontiers of nucleophilic addition of alcohols to alkenes

• Fabienne Speck,
• David Rombach and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 52–59, doi:10.3762/bjoc.15.5

• transfer followed by the intracage back-electron transfer, since triethylamine is no longer needed (vide infra). The evaluation of both the optical and electrochemical properties of the prepared phenothiazine derivatives 1–11 leads to the conclusion that only the dialkylamino derivatives 2, 10 and 11 come

Two novel blue phosphorescent host materials containing phenothiazine-5,5-dioxide structure derivatives

• Feng-Ming Xie,
• Qingdong Ou,
• Qiang Zhang,
• Jiang-Kun Zhang,
• Guo-Liang Dai,
• Xin Zhao and
• Huai-Xin Wei

Beilstein J. Org. Chem. 2018, 14, 869–874, doi:10.3762/bjoc.14.73

• time, the photophysical properties, electrochemical properties and their thermal stability were studied and the expected results were obtained. Results and Discussion Synthesis and theoretical calculations The synthesis route for CEPDO and CBPDO is shown in Scheme 1. The detailed synthesis procedures

• CEPDO and CBPDO are expected to be applied to PhOLED as a blue phosphorescent host material. Electrochemical properties The electrochemical properties of CEPDO and CBPDO were studied by cyclic voltammetry (CV) measurements in deoxygenated DCM solution with 0.1 M tetrabutylammonium hexafluorophosphate as