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

• (C6F5)3 (BCF) to bind to nitrogen atoms at the basic site a of π-conjugated polymer, providing a simple strategy to regulate the optical properties of the A–D–A chromophore with charge transfer excited state properties [28]. In 2019, Wang et al. constructed a novel exciplex system by using the Lewis

• substituents on the benzene rings of B(C6F5)3 is responsible for its stronger Lewis acidity compared to B(C6H5)3, and reacted efficiently with the basic fluorescent materials. In 2011, Hayashi investigated the modification of pyridyl-conjugated polymer films with the Lewis acid BF3 [31]. Through repeated acid

• with BF3, BBr3, and AlCl3, respectively, mixed in the low bandgap conjugated polymer materials. This is ascribed to the formation of Lewis acid–base adducts [34]. Fluorescent materials as electron donors Hancock et al. compared the PL and EL spectra of the π-conjugated heterocyclic oligomer 6,6’-bis(2

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

• , in the NIR region. In addition, the azulene-2,1,3-benzothiadiazole containing D–A-type copolymers have also been used in photovoltaic device applications [43]. Azulene-carbazole copolymers The same group [44] also synthesized the azulene-carbazole-conjugated polymer 140 and a set of terpolymers 141

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

Selective recognition of ATP by multivalent nano-assemblies of bisimidazolium amphiphiles through “turn-on” fluorescence response

• Rakesh Biswas,
• Surya Ghosh,
• Shubhra Kanti Bhaumik and
• Supratim Banerjee

Beilstein J. Org. Chem. 2020, 16, 2728–2738, doi:10.3762/bjoc.16.223

• the receptor with their complementary binding partners in the target analyte [15]. One of the ways to design multivalent systems is to connect the receptors through covalent linkages. Conjugated polymers and conjugated polymer electrolytes are prominent examples of covalently constructed multivalent

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

• conjugated polymer and applied the material for singlet oxygen photosensitisation [131]. Both of these were applied as HPCats in a commercial flow reactor for photocatalysis. Whilst flow chemistry is generally used to enhance the efficiency of HPC processes, we recently demonstrated that it can also enhance

Room-temperature Pd/Ag direct arylation enabled by a radical pathway

• Amy L. Mayhugh and
• Christine K. Luscombe

Beilstein J. Org. Chem. 2020, 16, 384–390, doi:10.3762/bjoc.16.36

• number average molecular weight of 14 kg/mol, although in 9% yield [7]. Room-temperature DArP would improve the simplicity of conjugated polymer synthesis, and reduce the energy requirements. Small molecule reactions can help predict a method’s utility in polymerizations, as DArP proceeds through a step

• paper, we investigated the mechanism of room-temperature direct arylation and DArP by extending the method reported by Larrosa to synthesize a conjugated polymer, polyindole (PIn). Small molecule mechanistic studies were undertaken that will help future development of mild, efficient DArP conditions

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

• Xiao Huang,
• Li Yang,
• Rikard Emanuelsson,
• Jonas Bergquist,
• Maria Strømme,
• Martin Sjödin and
• Adolf Gogoll

Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265

• research on functionalized polypyrroles [14] and polythiophenes [15] demonstrates that the attachment of functionalized pendant groups to the conjugated polymer backbone provides access to novel properties and applications. An EDOT building block to which highly functionalized pendants can easily be

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

• spectra (see Supporting Information File 1, Figures S4–S6) show four strong peaks in the range 1300 cm−1 to 1700 cm−1, associated with stretching modes of the conjugated polymer backbone. These peaks can be readily assigned to the P3OT and F-P3OT blocks of the polymer chain by comparison with the

• thermal stability of the diblock over the blend sample in this case does not appear to affect the melting temperature significantly, rather the stabilization relates to the molecular conformational order and particularly the planarity of the conjugated polymer backbone. This result indicates that the

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• substitution at the pyrrolic phenylacetylene moieties. The later complexes are expected to be stronger electron acceptors than Zn(WS3)2, and may enable charge transfer from other conjugated polymer donors that have lower energy levels than poly(3-hexylthiophene) (P3HT). Keywords: dye; fluorine; near-IR

• expected to be stronger electron acceptors than Zn(WS3)2, and may enable charge transfer from other conjugated polymer donor that have lower energy levels than P3HT. Results and Discussion Synthesis The synthesis of ADP was carried out according to literature procedures [9][33]. The ADP-analogs with

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• had two limitations. The second issue we had was lack of choices in emission color – blue and green are easy, yellow is challenging, and getting a red conjugated polymer with a respectable quantum yield is nigh impossible. We had an idea, however, that we could use multi-channel sensing to increase

Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

• Desta Gedefaw,
• Marta Tessarolo,
• Margherita Bolognesi,
• Mario Prosa,
• Renee Kroon,
• Wenliu Zhuang,
• Patrik Henriksson,
• Kim Bini,
• Ergang Wang,
• Michele Muccini,
• Mirko Seri and
• Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

• a blend of π-conjugated polymer (electron donor) and fullerene derivative (electron acceptor) sandwiched between two electrodes (anode and cathode) [1][2][3][4]. Noticeable achievements have been recorded in terms of the power conversion efficiency (PCE) of lab-scale single junction BHJ PSCs

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• design of gelators [33][34]. Combining the exceptional donor strength of TTF and excellent film-forming properties of a conjugated polymer (CP) opens up the possibility to create promising materials with interesting redox behaviour. So far the TTF unit has been used for redox modification of various CP

• , the polymer 34 exhibited an absorption band with a maximum at ca. 490 nm and extending to ca. 736 nm, with an optical band gap of 1.69 eV (Table 2). For a simple π-conjugated polymer the difference between the oxidation and reduction onsets constitute the electrochemical band gap [74][75]. For polymer

Chiroptical properties of 1,3-diphenylallene-anchored tetrathiafulvalene and its polymer synthesis

• Masashi Hasegawa,
• Junta Endo,
• Seiya Iwata,
• Toshiaki Shimasaki and
• Yasuhiro Mazaki

Beilstein J. Org. Chem. 2015, 11, 972–979, doi:10.3762/bjoc.11.109

• -diphenyl allene unit [15]. In addition, Fallis and co-workers synthesized a cyclic oligoallene based on a chiral 1,3-diphenylallene [16]. More recently, Kijima and co-workers reported the use of a racemic 1,3-diphenylallene framework as a new building block for a π-conjugated polymer [17]. However, there

• . Previously, a racemic conjugated polymer in the literature was prepared by a Suzuki–Miyaura or Yamamoto coupling reaction from (rac)-8 [17]. In contrast, to the best of our knowledge, there is no example of a chiral polymer based on the 1,3-diphenylallene frameworks that can be a unit of copolymer with

Peptide–polymer ligands for a tandem WW-domain, an adaptive multivalent protein–protein interaction: lessons on the thermodynamic fitness of flexible ligands

• Katharina Koschek,
• Vedat Durmaz,
• Oxana Krylova,
• Marek Wieczorek,
• Shilpi Gupta,
• Martin Richter,
• Alexander Bujotzek,
• Christina Fischer,
• Rainer Haag,
• Christian Freund,
• Marcus Weber and
• Jörg Rademann

Beilstein J. Org. Chem. 2015, 11, 837–847, doi:10.3762/bjoc.11.93

• . Moreover, attachment of bioactive peptides to polymers strongly enhanced their stability and protected them from proteolysis [7][8]. The construction of peptide-polymer conjugates with additional cell-penetrating peptides attached [9] enabled the smooth intracellular delivery of the conjugated polymer; as

Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin

• Jun Terao,
• Yohei Konoshima,
• Akitoshi Matono,
• Hiroshi Masai,
• Tetsuaki Fujihara and
• Yasushi Tsuji

Beilstein J. Org. Chem. 2014, 10, 2800–2808, doi:10.3762/bjoc.10.297

• ; permethylated cyclodextrin; [3]rotaxane; Introduction Insulated molecular wires (IMWs) [1][2], which feature π-conjugated polymer chains covered by protective sheaths, have attracted considerable attention as next-generation mono-molecular electronic devices because of their potential conductivity and

• synthesis of π-conjugated polymer-based IMWs using CD derivatives involve (I) threading π-conjugated polymers through CD [8][9] using a method developed by Harada for the synthesis of a polyrotaxane [10], (II) polymerization of pseudo [2]rotaxane monomer formed by self-inclusion of a π-conjugated guest with

• CD [11], and (III) copolymerization of the thus-formed pseudorotaxane with linker molecules [12]. These polymers are soluble in water but generally insoluble in organic solvents; this is because the hydrophilic CD covers the organic soluble π-conjugated polymer chains [13]. Uncovered sites are also

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

• interpenetrating network they form within a bulk heterojunction (BHJ), has led to intense research directed towards the synthesis of conjugated polymers for bulk heterojunction organic photovoltaics (OPVs) [1][2][3]. In these devices, the conjugated polymer acts as an electron donor and a soluble fullerene, most

The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

• Aurica Farcas,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert,
• Flavian Farcas,
• Iuliana Stoica and
• Anton Airinei

Beilstein J. Org. Chem. 2014, 10, 2145–2156, doi:10.3762/bjoc.10.222

• macrocycle molecules has been employed as an alternative approach to achieve the control of aggregation and to improve the photophysical and morphological characteristics [13]. In the past years, it has been demonstrated that the encapsulation of conjugated polymer into macrocycle cavities leads to an

• and their values of the α parameter and the grain diameter reflect the chemical changes of the conjugated polymer surfaces. Thus, the 4a film surface shows smaller grains with an average diameter of 86 ± 8 nm. Furthermore, the relative uniform grain size dispersion induces the lower value of α (0.229

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

• Helga Seyler,
• Jegadesan Subbiah,
• David J. Jones,
• Andrew B. Holmes and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

• mixing of reagents, boosting reaction rates, and safe handling of reactive intermediates. Using a commercial continuous-flow tube reactor [19], we have already demonstrated multigram synthesis of fullerene derivatives by cycloaddition reactions [11] as well as rapid conjugated-polymer synthesis using

The chemistry of bisallenes

• Henning Hopf and
• Georgios Markopoulos

Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• characteristic properties of the polymers are described. Potential applications in the field of organic electronic materials such as light emitting diodes, organic solar cells and organic field effect transistors are discussed. Keywords: conjugated polymer; diketopyrrolopyrrole; electroluminescence

• nematic and smectic enantiotropic phases. In the same year, the first study on electroluminescent (EL) properties of a DPP-containing conjugated polymer was reported by Beyerlein et al. [28] who studied a DPP-dialkoxyphenylene copolymer in a multilayer device of ITO/DPP-polymer/OXD7/Ca/-Mg:Al:Zn and

Synthesis of thienyl analogues of PCBM and investigation of morphology of mixtures in P3HT

• Fukashi Matsumoto,
• Kazuyuki Moriwaki,
• Yuko Takao and
• Toshinobu Ohno

Beilstein J. Org. Chem. 2008, 4, No. 33, doi:10.3762/bjoc.4.33

• ]. Recently, bulk heterojunction solar cells consisting of a conjugated polymer (donor) and fullerene derivatives (acceptors) have inspired much scientific research owing to these reasons [8][9]. In this research, it has been demonstrated that the PV cells based on regio-regular poly(3-hexylthiophene) (P3HT

• heterojunction PV devices and the first drastic improvement in device efficiency was achieved by replacing the original donor, poly{[2-methoxy-5-(3,7-dimethyloctyloxy)-p-phenylene]vinylene} (MDMO-PPV, Figure 1), with a high-mobility conjugated polymer, P3HT [17][18][19][20]. However, sufficient investigations