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

Indenopyrans – synthesis and photoluminescence properties

• Andreea Petronela Diac,
• Ana-Maria Ţepeş,
• Albert Soran,
• Ion Grosu,
• Anamaria Terec,
• Jean Roncali and
• Elena Bogdan

Beilstein J. Org. Chem. 2016, 12, 825–834, doi:10.3762/bjoc.12.81

• trifluoromethylated heterocycles, such as indone and carbostyril derivatives. Based on their important biological functions in nature and the synthetic potential of α-pyrones for the construction of a variety of fluorescent heteroarenes, we decided to synthesize and study the optoelectronic properties of some indeno

A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations

• Xinlong Pang,
• Chao Chen,
• Ming Li and
• Chanjuan Xi

Beilstein J. Org. Chem. 2015, 11, 2365–2369, doi:10.3762/bjoc.11.258

• catalytic reactions. Recently, the conjugation of different types of azaheterocycles in the same molecule has received considerable attention since the resulting ring-fused molecules often show unique organic optoelectronic properties and bioactive activities [1][2]. Among them, benzimidazo[1,2-c

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• % when combined with poly(3-hexylthiophene) [30][31]. 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY, 2), and its derivatives have been widely used in the last two decades due to their outstanding chemical and optoelectronic properties [32][33][34]. BODIPY derivatives are promising compounds to be

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

• anticipated, altering the trialkylsilyl group has very little effect on the optoelectronic properties of the conjugated scaffold (Table 2). All molecules have two strong absorptions around 310 and 330 nm, with a much weaker, broad absorption in the 450–550 nm range. Electrochemistry shows two reversible

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

• Anastasia S. Kostyuchenko,
• Vyacheslav L.Yurpalov,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2014, 10, 1596–1602, doi:10.3762/bjoc.10.165

• by consequence their electron affinity (EA) and ionization potential (IP) are not appropriate [2]. Since these two parameters determine the redox, spectroscopic, electronic and optoelectronic properties of oligothiophenes, their tuning is of crucial importance in any design of new organic

Enhancement of efficiency in organic photovoltaic devices containing self-complementary hydrogen-bonding domains

• Rohan J. Kumar,
• Jegadesan Subbiah and
• Andrew B. Holmes

Beilstein J. Org. Chem. 2013, 9, 1102–1110, doi:10.3762/bjoc.9.122

• ] followed by a Knoevenagel condensation provided the target compound 2 in excellent yield. The solubilizing strategy of incorporating alkyl groups on the thiophene unit provided the compound with excellent solubility in a wide range of common solvents. Optoelectronic properties In chloroform solution the UV

Synthesis, photophysical and electrochemical characterization of terpyridine-functionalized dendritic oligothiophenes and their Ru(II) complexes

• Amaresh Mishra,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2013, 9, 866–876, doi:10.3762/bjoc.9.100

• oligomers and polymers are amongst the best-studied π-conjugated systems in the past few decades because of their tunable optoelectronic properties [6][7][8]. Furthermore, transition-metal complexes offer significant advantages such as long-lived luminescent excited states, high chemical and photochemical

Synthesis and characterization of low-molecular-weight π-conjugated polymers covered by persilylated β-cyclodextrin

• Aurica Farcas,
• Ana-Maria Resmerita,
• Andreea Stefanache,
• Mihaela Balan and
• Valeria Harabagiu

Beilstein J. Org. Chem. 2012, 8, 1505–1514, doi:10.3762/bjoc.8.170

• , electronic and thermal properties [11][12][13][14][15][16][17][18]. However, as a consequence of intramolecular interactions, these synthetic methods are often accompanied by undesirable side effects influencing the optoelectronic properties, e.g., red shifting or lower fluorescence. As a route to candidate

Thiophene-based donor–acceptor co-oligomers by copper-catalyzed 1,3-dipolar cycloaddition

• Stefanie Potratz,
• Amaresh Mishra and
• Peter Bäuerle

Beilstein J. Org. Chem. 2012, 8, 683–692, doi:10.3762/bjoc.8.76

• –donor type, in which thiophene moieties work as donor and 1,2,3-triazoles as acceptor units. In this respect, terminally ethynylated (oligo)thiophenes were coupled to halogenated (oligo)thiophenes in the presence of sodium azide and a copper catalyst. Optoelectronic properties of various thiophene-1,2,3

Syntheses and properties of thienyl-substituted dithienophenazines

• Annemarie Meyer,
• Eva Sigmund,
• Friedhelm Luppertz,
• Gregor Schnakenburg,
• Immanuel Gadaczek,
• Thomas Bredow,
• Stefan-S. Jester and
• Sigurd Höger

Beilstein J. Org. Chem. 2010, 6, 1180–1187, doi:10.3762/bjoc.6.135

• ]. In addition, fused bithiophenes with an enforced planarity, and therefore reduced optical gaps, and an increased π–π overlap of the polycyclic molecule backbone have entered various fields of organic electronics [9][10][11][12][13]. Apart from their optoelectronic properties, linear and branched as

Self-assembly and semiconductivity of an oligothiophene supergelator

• Pampa Pratihar,
• Suhrit Ghosh,
• Vladimir Stepanenko,
• Sameer Patwardhan,
• Ferdinand C. Grozema,
• Laurens D. A. Siebbeles and
• Frank Würthner

Beilstein J. Org. Chem. 2010, 6, 1070–1078, doi:10.3762/bjoc.6.122

• bisimides [10][11][12], acenes [13][14] and merocyanines [15][16] have been studied in recent years. Self-assembly of various oligothiophene derivatives have been extensively investigated on account of their semiconducting and optoelectronic properties [17]. Feringa and co-workers reported organogels based