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

• of click-type [2 + 2] cycloaddition (CA)–retroelectrocyclization (RE) reactions, offering means for preparing these coveted push–pull chromophores [7]. A review conducted in 2023 comprehensively explored the optoelectronic properties of TCBDs along with their photovoltaic applications [8]. The

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

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

• for use in cutting-edge technologies. In particular, acenes, a subgroup of polycyclic aromatic compounds, are sought-after synthetic targets due to their remarkable optoelectronic properties which stem from their π-conjugation and planar structure. Despite all these promising characteristics, acenes

• antiaromatic four-membered ring. This review gives a brief overview of the methods used in the synthesis of biphenylenes and summarizes the recent studies on biphenylene-containing polycyclic conjugated compounds, elucidating their synthesis, and distinct optoelectronic properties. Keywords: acenes

• establish an alternative synthetic approach to the existing methods for biphenylene synthesis described in the literature, rather than focusing on the optoelectronic properties of the resulting compounds. Small quantities of the key starting material benzocyclobutene-1,2-dione (BBD, 13) were obtained

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

• chemistry offers a cost-effective and time-efficient means of screening and selecting promising candidates for experimental exploration. Bhattacharya et al. employed density functional theory (DFT) approach to explore structural modulation for tuning the optoelectronic properties of Qx13. Their designed

• their optoelectronic properties to highlight the potential of their experimental exploration [33]. The introduction of an electron-withdrawing group has been shown to be a key strategy for enhancing intermolecular interactions and improving the optical absorption, molecular packing, and charge transport

• absorption, improved carrier mobility, and reduced charge recombination of NFAs. Qx21, bearing chlorine atoms on the end groups as opposed to Qx20, showed superior optoelectronic properties and a PCE of 12.32% with PBDB-T as donor in OSC device [34]. The same group explored side-chain engineering and

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

• without lengthy extension of their π-conjugation systems due to a broadening of both the valence and the conduction bands and a consequent narrowing of the energy gap [22][23][24][25]. The D–A characters also offer a tunability of optoelectronic properties such as energy levels, optical bandgap (Eg), and

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

• 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

• are reported for the design strategy used, their synthesis, optoelectronic properties, electrochemical properties, and processability from ethyl acetate for thin film formation. Lastly, each new CIL material was tested in conventional OPVs by processing with ethyl acetate, a green solvent [20][21][22

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• derivatives have attracted increasing attention due to their specific optoelectronic properties [5][29]. HBC thus generally serves as a reference structure or building block to construct chiral NGs which are currently receiving a lot of interest in carbon-based materials science. This review will mainly focus

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

• Hengjia Liu and
• Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

• coordination between Lewis acids and bases, which can finely adjust the optoelectronic properties of the fluorescent molecules, such as band gaps, peak wavelengths, and even frontier molecular orbitals if bound together [20]. The traditional way to manipulate the optoelectronic properties of the emitters

• optoelectronic properties of a fluorene-based copolymer with an sp2 nitrogen heteroatom via supramolecular coordination [33]. The PL emission in solution showed an obvious red-shifted profile. The polymer LED with different molar equivalents of Lewis acids was investigated. The EL peak wavelength was gradually

• with the Lewis acids discussed in this review and thus lead to a significant shift of their optoelectronic properties. It has been confirmed that organic molecules containing pyrimidine, pyrazine, and indole groups display similar interactions upon the addition of Lewis acids [40][41][42]. Lewis acid

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

• electroluminescence, with λEL going from 449 nm for CzTRZ to 490 nm for 33TCzTTrz. In this work, we utilized a similar strategy to assess the change in optoelectronic properties and device performance of the compound DICzTRZ (Figure 2) compared to our recently reported ICzTRZ study [14]. We note that the effective

• 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

• optoelectronic properties [32][35][36][37]. Acridines, as aza-analogues of anthracene have obtained much attention in the field of organic light emitting diodes [38][39][40][41]. While considerable attention has been devoted to the photophysical properties of acridines, not much work has been reported related to

• their optoelectronic properties, the search for new candidates is of ongoing interest. Recently, considerable attention has been given to acridines in our laboratory and we developed new synthetic methods for dibenzoacridines and acridones based on Pd-catalyzed cross-coupling reactions [55][56]. More

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

• possibility of varying optoelectronic properties, and good solubility in a wide range of solvents [59][60][61]. In this regard, the most studied and promising are π-conjugated polymer structures based on sulfur, oxygen, nitrogen, and selenium heterocyclic compounds [62][63]. One of the systems for creating

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2021, 17, 1374–1384, doi:10.3762/bjoc.17.96

• interdisciplinary interest from both fundamental as well as applied viewpoint on account of their wonderful optoelectronic properties. The scientific interest in two-dimensional star-shaped PAHs particularly in truxene architectures arises because of their high thermal stability, exceptional solubility and ease

Exploring the possibility of using fluorine-involved non-conjugated electron-withdrawing groups for thermally activated delayed fluorescence emitters by TD-DFT calculation

• Dongyang Chen and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 210–223, doi:10.3762/bjoc.17.21

• explore their potential computationally within TADF emitter design. We cross-compare their optoelectronic properties with analog materials using well-studied conjugated electron-withdrawing groups (cyano, benzophenone, and triazine). We investigated two families of structures. The first family consists of

Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring

• Daria I. Tonkoglazova,
• Anna V. Gulevskaya,
• Konstantin A. Chistyakov and
• Olga I. Askalepova

Beilstein J. Org. Chem. 2021, 17, 11–21, doi:10.3762/bjoc.17.2

• polycyclic π-systems additionally contributes to altering electronic structure and helps to fine tune optoelectronic properties [1][2][3][4][5][6][7][8][9][10][11][20][35][36][37]. The last decades highlighted heterohelicenes, incorporating one or two carbazole fragments, as a very attractive class of

Synthesis and characterization of S,N-heterotetracenes

• Astrid Vogt,
• Florian Henne,
• Christoph Wetzel,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2020, 16, 2636–2644, doi:10.3762/bjoc.16.214

• . 250, 64293 Darmstadt, Germany 10.3762/bjoc.16.214 Abstract The synthesis and optoelectronic properties of novel S,N-heterotetracenes consisting of fused heterocyclic thiophene and pyrrole rings are presented. Tetracyclic and benzannulated derivatives with a varying number and sequence of sulfur and

• reaction; optoelectronic properties; S,N-heteroacene; structure–property relationship; Introduction Thienoacenes and related S,N-heteroacenes have been developed to important π-conjugated systems mainly for application as p-type semiconductor in organic electronic devices with excellent results [1][2][3

• –property relationships showing the influence of the number and sequence of pyrrole rings. The highly planar π-conjugated systems revealed interesting structural features such as nearly complete bond length equalization and S–S and S–π dipolar interactions in the solid state. Due to tunable optoelectronic

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

• MIMs based on two 24-crown-8 ethers functionalized with TTF TTFC8 [35][36] and exTTFC8 [37] (Figure 1). Several TTFC8-derived molecular assemblies have been studied and provided access to new switching modes [35][36][38] and emergent optoelectronic properties [35][36][39][40], demonstrating the great

• differential pulse voltammetry (DPV) and compared to those of their corresponding pseudo[2]rotaxanes. Additionally, we report the synthesis of a novel NDI-[2]rotaxane and study the impact of the mechanical bond on the optoelectronic properties of the NDI unit by CV and spectroelectrochemical measurements

• optoelectronic properties of the TTF unit [35], yet for exTTFC8 the [2]rotaxane shows very similar properties as compared to the free macrocycle [37]. As NDIC8 and the A1·PF6@NDIC8 pseudo[2]rotaxane also reveal distinctly different electrochemical potentials, we investigated the impact of mechanical bonding on

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

• Péter Bagi,
• Réka Herbay,
• Nikolett Péczka,
• Zoltán Mucsi,
• István Timári and
• György Keglevich

Beilstein J. Org. Chem. 2020, 16, 818–832, doi:10.3762/bjoc.16.75

• -coupled transformations [18][22][23]. Polycyclic compounds incorporating a P-heterocyclic moiety are of special importance due to their optoelectronic properties and applications [24][25][26]. Moreover, a few biologically active 5-membered P-heterocyclic derivatives are also known, which showed promising

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

• extensively developed to tune the optoelectronic properties [21]. Therefore, the development of more efficient and shorter step synthetic methods for the BODIPY derivatives, such as direct C–H functionalizations (e.g., arylation [22][23][24][25][26][27][28], annulation [29], olefination [30], styrylation [31

Six-fold C–H borylation of hexa-peri-hexabenzocoronene

• Mai Nagase,
• Kenta Kato,
• Akiko Yagi,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37

• -catalyzed six-fold C–H borylation of HBC was successfully achieved by screening solvents. The crystal structure of hexaborylated HBC was confirmed via X-ray crystallography. Optoelectronic properties of the thus-obtained hexaborylated HBC were analyzed with the support of density functional theory

• high solubility of 1. In order to analyze the optoelectronic properties of 1, the UV–vis absorption spectra, fluorescence spectrum, absolute fluorescence quantum yield and fluorescence lifetime were measured (Figure 4a and Figure S1, Supporting Information File 1). In comparison with the absorption

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

• benzoquinone (BQ)-based charge-transfer (CT) derivatives in good yields. The optoelectronic properties of these compounds were explored both theoretically and experimentally and correlations to their structures were identified as a function of the nature and position of the donor group (meta and para) attached

• compounds (Figure 1), with the aim of exploring their optoelectronic properties. Results and Discussion Synthesis We initiated our studies by synthesizing monofunctionalized donor–acceptor compounds 2–4, using the Pd(II)-catalyzed direct C–H functionalization method described below (Scheme 2). To our

• 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

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• displaying a panchromatic absorption with an extension to the near-infrared (NIR) range. An innovative synthetic approach for preparing the 2,3,5,6-tetramethyl-BODIPY unit is disclosed, and a versatile way to further functionalize this unit has been developed. The optoelectronic properties of the two dyes

• even bulk heterojunction solar cells [19][20] or DSSCs [21][22]. In this articl we report an innovative synthetic approach for synthesizing 2,3,5,6-tetramethyl-BODIPY compounds and a way to further functionalize such cores has been developed. The optoelectronic properties of the functional molecules

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

• of the geometric and electronic structure of the heterotriacenes. The optoelectronic properties were determined and valuable structure–property relationships were deduced giving insight into the role of the number and relative position of the S and Se heteroatoms in the equally long fused conjugated

• crucial cyclization steps to the stable and soluble fused systems were achieved by copper-catalyzed C–S and C–Se coupling/cyclization reactions. Structures and packing motifs in the solid state were elucidated by single crystal X-ray analysis and XRD powder measurements. Comparison of the optoelectronic

• properties provides interesting structure–property relationships and gives valuable insights into the role of heteroatoms within the series of the heterotriacenes. Electrooxidative polymerization led to the corresponding poly(heterotriacene)s P2–P4. Keywords: conducting polymer; C–S coupling; C–Se coupling

Synthesis of dipolar molecular rotors as linkers for metal-organic frameworks

• Sebastian Hamer,
• Fynn Röhricht,
• Marius Jakoby,
• Ian A. Howard,
• Xianghui Zhang,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1331–1338, doi:10.3762/bjoc.15.132

• region and to implement interesting optoelectronic properties into the final MOF structures [37][38][39][40][41]. Prior to synthesis, we calculated the dipole moments and barriers to rotation of the isolated rotors 1–5 (Table 1 and Figure 1). The rotational barriers of all rotors are below 2 kcal mol−1

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

• optoelectronic properties of the molecules. Photochemical methods have allowed to overcome some of the current limitations in thermally driven chemistry and to substitute conventional energy demanding chemistry by highly sustainable photochemical methods [3][4][5][6][7][8][9][10][11][12]. Phenothiazines have

• up with an estimated excited state reduction potential capable of reducing α-methylstyrene (13a). The optoelectronic properties and the excited state reduction potential of Ered(2+·/2*) = −2.5 V of dimethylamino compound 2 that is close to the reduction potential of the substrate 13a encouraged us to

Effects of solvent additive on “s-shaped” curves in solution-processed small molecule solar cells

• John A. Love,
• Shu-Hua Chou,
• Ye Huang,
• Guilllermo C. Bazan and
• Thuc-Quyen Nguyen

Beilstein J. Org. Chem. 2016, 12, 2543–2555, doi:10.3762/bjoc.12.249

• , reduced surface recombination, and interfacial defects leading to traps; device simulations have shown that all of these could indeed result in the s-shape behavior [23][24][25][26][27][28][29][30]. Herein we describe the development of a novel small molecule system with nearly ideal optoelectronic

• properties, which unfortunately results in s-shaped J–V curves and poor performance. We show that this is due to non-ideal phase separation, specifically a preferential migration of the electron acceptor to the bottom anode interface. This can, however, be mitigated through appropriate processing, using a

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

• accounting for the 1H NMR ratios of H to F blocks. Optoelectronic properties Our previous study on fluorinated poly(3-alkylthiophene) demonstrated that backbone fluorination leads to a ca. 0.3 eV increase in the ionisation potential (IP) compared to the non-fluorinated polymer [42]. In order to probe this

• polymer backbone through fluorination on the physical and optoelectronic properties of the P3OT system, two block copolymers were synthesized via sequential monomer addition under by Kumada catalyst transfer polymerisation (KCTP) conditions. Diblock polymers with a large and small F-P3OT block were