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

• promising synthetic tool to access a wider variety of π-conjugated polycyclic structures and thus to expand the potentialities of the “precursor approach” for further improvements of molecular materials’ performances. This review gives an overview of synthetic strategies towards π-CPCs involving the

• heteroatom-based counterparts, have attracted the attention of the scientific community for two centuries already. Initially, major interest resulted from their structural, optical and electronic properties at the molecular level, but the last decades witnessed the rise of molecular materials and π

• this route, the extrusion of chalcogen fragments appears as a highly promising synthetic tool to complement the retro-Diels–Alder and decarbonylation reactions mostly exploited up to now, and thus to expand the potentialities of the “precursor approach” for further improvements of molecular materials

Catalytic multi-step domino and one-pot reactions

• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

• Svetlana B. Tsogoeva Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus Fiebiger-Straße 10, 91058 Erlangen, Germany 10.3762/bjoc.20.25 Keywords: domino reactions

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

• [14], PDINO [14], and PDINN [15] (Figure 1), which have realized PCEs of ≈19% [6], ≈17% [16], ≈15% [17], and ≈17% [15], respectively, when implemented as CILs in conventional OPVs. While challenges exist for polymeric materials due to batch-to-batch variations, molecular materials are advantageous as

Light-responsive rotaxane-based materials: inducing motion in the solid state

• Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

• molecular materials, the development of a wide variety of suitable compounds is essential. The use of stimuli-responsive molecules has paved the way for the preparation of advanced functional materials [6][7][8][9][10]. In this scenario, mechanically interlocked molecules (MIMs) have postulated as ideal

• Photoresponsive rotaxane discrete crystals A complete understanding of the crystallization mechanisms accompanied by a rational design can lead to the obtention of crystalline molecular materials which allow the dynamics of the counterparts to take place [35][36][37]. Indeed, the motion of the cyclic counterparts

• . Flipping motions were induced enhancing the irradiation power to 12 mW. Noteworthy, these crystals showed a 9600 times higher weight ratio than its crystal weight due to the bending and expansion experienced by these crystalline molecular materials. These nanomachines are useful in the development of small

Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups

• Ita Hajdin,
• Romana Pajkert,
• Mira Keßler,
• Jianlin Han,
• Haibo Mei and
• Gerd-Volker Röschenthaler

Beilstein J. Org. Chem. 2023, 19, 541–549, doi:10.3762/bjoc.19.39

• Ita Hajdin Romana Pajkert Mira Kessler Jianlin Han Haibo Mei Gerd-Volker Roschenthaler School of Science, Constructor University Bremen gGmbH, Campus Ring 1, Bremen 28759, Germany Center for Molecular Materials, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany Jiangsu Co

Ferrocenoyl-adenines: substituent effects on regioselective acylation

• Mateja Toma,
• Gabrijel Zubčić,
• Jasmina Lapić,
• Senka Djaković,
• Davor Šakić and
• Valerije Vrček

Beilstein J. Org. Chem. 2022, 18, 1270–1277, doi:10.3762/bjoc.18.133

• ferrocene–nucleobase conjugates [4], which are known to exhibit anticancer [5][6][7], antibacterial [8][9][10], or antitrypanosomal activity [11], but also may serve as electrochemical biosensors [12][13], self-assembled molecular materials [14][15], decorations of carbon tubes and nanomaterials [16][17

Continuous flow synthesis of azobenzenes via Baeyer–Mills reaction

• Jan H. Griwatz,
• Anne Kunz and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2022, 18, 781–787, doi:10.3762/bjoc.18.78

• usually gives similar or improved yields and eliminates the shortcomings in scalability. For the applications of ABs as molecular materials often larger amounts are required, for example, as active compounds in molecular solar thermal energy storage (MOST) systems. Therefore, we utilized the set-up for

• be prepared in high yields and large quantities which opens new possibilities for applications of AB as molecular materials in general. Flow setup for optimization of the Baeyer–Mills reaction with aniline (2a) and nitrosobenzene (3). In this setup the temperature of the tube reactor as well as the

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

• ]. Unfortunately, the electrochemistry of some compounds could not be determined under the conditions available to us. Therefore, computational investigations are particularly useful for understanding the trends of the electrochemical and photophysical properties of molecular materials. Density functional theory

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

• Alexander Zika and
• Franziska Gröhn

Beilstein J. Org. Chem. 2021, 17, 166–185, doi:10.3762/bjoc.17.17

• Alexander Zika Franziska Grohn Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM) and Bavarian Polymer Institute (BPI), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstr. 3, D-91058 Erlangen, Germany 10.3762/bjoc.17.17 Abstract Light- and

• Financial support of the German Science Foundation (DFG) and the Interdisciplinary Center for Molecular Materials (ICMM) is gratefully acknowledged.

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

• Si-Yuan Liu,
• Xin-Rui Wang,
• Man-Ping Li,
• Wen-Rong Xu and
• Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

• Department of Chemistry, Center for Molecular Materials (CM2), Bielefeld University, 33615 Bielefeld, Germany 10.3762/bjoc.16.207 Abstract A sugar-functionalized water-soluble tribenzotriquinacene derivative bearing six glucose residues, TBTQ-(OG)6, was synthesized and its interaction with C60 and C70

Synthesis of 6,13-difluoropentacene

• Matthias W. Tripp and
• Ulrich Koert

Beilstein J. Org. Chem. 2020, 16, 2136–2140, doi:10.3762/bjoc.16.181

• expanded π-systems and low HOMO–LUMO gaps with applications in different molecular-based organic electronics like OFETs, OLEDs or organic photovoltaics [1][2][3]. An advantage of organic molecular electronics over inorganic alternatives is the versatility in design of new molecular materials by

A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

• Ilya V. Taydakov,
• Yuliya M. Kreshchenova and
• Ekaterina P. Dolotova

Beilstein J. Org. Chem. 2018, 14, 3106–3111, doi:10.3762/bjoc.14.290

• MS measurements was provided by the Russian Foundation for Basic Research (grants No. 18-29-04029 and 18-02-00653). IVT is also grateful to Volkswagenstiftung (Project «Multifunctional molecular materials – bridging magnetism and luminescence»). The authors are thankful to Dr. Yu. Belousov (LPI) for

Non-metal-templated approaches to bis(borane) derivatives of macrocyclic dibridgehead diphosphines via alkene metathesis

• Tobias Fiedler,
• Michał Barbasiewicz,
• Michael Stollenz and
• John A. Gladysz

Beilstein J. Org. Chem. 2018, 14, 2354–2365, doi:10.3762/bjoc.14.211

• Tobias Fiedler Michal Barbasiewicz Michael Stollenz John A. Gladysz Department of Chemistry, Texas A&M University, PO Box 30012, College Station, Texas 77842-3012, USA Institut für Organische Chemie and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

Grip on complexity in chemical reaction networks

• Albert S. Y. Wong and
• Wilhelm T. S. Huck

Beilstein J. Org. Chem. 2017, 13, 1486–1497, doi:10.3762/bjoc.13.147

• Albert S. Y. Wong Wilhelm T. S. Huck Institute for Molecular Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands 10.3762/bjoc.13.147 Abstract A new discipline of “systems chemistry” is emerging, which aims to capture the complexity observed in natural

Synthesis of oligonucleotides on a soluble support

• Harri Lönnberg

Beilstein J. Org. Chem. 2017, 13, 1368–1387, doi:10.3762/bjoc.13.134

• oligonucleotides from small molecular materials. The underlying idea is to keep the growing oligonucleotide chain sufficiently hydrophobic to enable removal of the excess of building blocks, activators and wastes by water extraction, but still allow removal of highly hydrophobic substances, above all DMTrOMe, by

Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates

• Anna Wrona-Piotrowicz,
• Marzena Witalewska,
• Janusz Zakrzewski and
• Anna Makal

Beilstein J. Org. Chem. 2017, 13, 1032–1038, doi:10.3762/bjoc.13.102

• ; pyrene; thioamide; Introduction Direct functionalization of pyrene 1 has attracted a great deal of attention in recent years because it is the most straightforward route to novel organic molecular materials for optoelectronic devices (OLEDs, field-effect transistors, fluorescent sensors, dye lasers, etc

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

• Paul B. Geraghty,
• Calvin Lee,
• Jegadesan Subbiah,
• Wallace W. H. Wong,
• James L. Banal,
• Mohammed A. Jameel,
• Trevor A. Smith and
• David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

• devices with PTB7-Th resulting in high-performance OPV devices with up to 10.7% PCE. Keywords: molecular materials; nematic liquid crystal; organic solar cells; organic synthesis; p-type organic semiconductors; small molecule; Introduction Bulk heterojunction (BHJ) organic solar cells (OSC), a blend of

• p-type and n-type conjugated polymers or molecular materials (MM), have attracted significant attention as alternative solar cell technologies as they are light-weight, low-cost and offer the opportunity of cheaper manufacturing employing roll-to-roll printing processes [1][2][3]. Recent advances in

• -dependent DFT (TD-DFT) calculations were carried out on the optimized structures with PBE0/def2-TZVP level of theory based on our benchmark calculations (Supporting Information File 1, chapter S11). It is apparent in Figure 11 that as the BXR molecular materials increase in size the overlap of the HOMO and

Creating molecular macrocycles for anion recognition

• Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

• the surfaces of molecules to direct their hierarchical assembly into molecular materials. The discovery of tricarb’s 3D assembly at interfaces [8] is igniting this work. Our inclination to collaborate with theorists also opens up the chance to design those hierarchical assemblies using computer-aided

Tetrathiafulvalene-based azine ligands for anion and metal cation coordination

• Awatef Ayadi,
• Aziz El Alamy,
• Olivier Alévêque,
• Magali Allain,
• Nabil Zouari,
• Mohammed Bouachrine and
• Abdelkrim El-Ghayoury

Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149

• derivatives [1] has been initiated by the high electrical conductivity discovered in a chloride salt of TTF [2] and metallic behavior in the charge-transfer complex with 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) [3]. These systems have played a major role for the preparation of molecular materials designed

• biggest challenges in materials science is devoted to the preparation of multifunctional molecular materials that can potentially exhibit, in solution and/or in solid state, synergy or coexistence between two or more different physical properties. In order to address this issue, many efforts have been

Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones

• Flavia Pop and
• Narcis Avarvari

Beilstein J. Org. Chem. 2015, 11, 1105–1111, doi:10.3762/bjoc.11.124

• conformation. Cyclic voltammetry measurements indicate fully reversible oxidation in radical cation and dication species. Keywords: chirality; crystal structures; molecular materials; sulfones; tetrathiafulvalenes; Introduction Chiral tetrathiafulvalene (TTF) derivatives have been addressed for the first

Copper ion salts of arylthiotetrathiafulvalenes: synthesis, structure diversity and magnetic properties

• Longfei Ma,
• Jibin Sun,
• Xiaofeng Lu,
• Shangxi Zhang,
• Hui Qi,
• Lei Liu,
• Yongliang Shao and
• Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 850–859, doi:10.3762/bjoc.11.95

• difference on electrical transport properties. Meanwhile, the modification on TTF, particularly introducing aromatic substituents onto the TTF core, is one of the key strategies to explore functional molecular materials. The resulting TTFs have been employed as electrochemically active units in

TTFs nonsymmetrically fused with alkylthiophenic moieties

• Rafaela A. L. Silva,
• Bruno J. C. Vieira,
• Marta M. Andrade,
• Isabel C. Santos,
• Sandra Rabaça,
• Dulce Belo and
• Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 628–637, doi:10.3762/bjoc.11.71

• ; supramolecular chemistry; tetrathiafulvalene (TTF); thiophene; Introduction Since the discovery of the first organic metals and superconductors the field of electronic molecular materials has been largely dominated by derivatives of the organic donor tetrathiafulvalene (TTF) [1]. More than one thousand TTF

Aryl substitution of pentacenes

• Andreas R. Waterloo,
• Anna-Chiara Sale,
• Dan Lehnherr,
• Frank Hampel and
• Rik R. Tykwinski

Beilstein J. Org. Chem. 2014, 10, 1692–1705, doi:10.3762/bjoc.10.178

• Andreas R. Waterloo Anna-Chiara Sale Dan Lehnherr Frank Hampel Rik R. Tykwinski Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054 Erlangen, Germany Department of Chemistry, University of

Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins

• G. Gangadhararao,
• Ramesh Kotikalapudi,
• M. Nagarjuna Reddy and
• K. C. Kumara Swamy

Beilstein J. Org. Chem. 2014, 10, 996–1005, doi:10.3762/bjoc.10.99

• ; propargyl alcohols; Introduction Allenes, by virtue of cumulative double bonds that facilitate reactions with diverse classes of substrates, are versatile building blocks from a synthetic perspective [1][2]. They are also found in many natural products, pharmaceuticals [3] and molecular materials [4]. Thus