Life lessons

• Jonathan R. Nitschke

Beilstein J. Org. Chem. 2015, 11, 2350–2354, doi:10.3762/bjoc.11.256

• sixth – usually chloride – in its center [27]; Figure 2c illustrates a FeII12L12 pseudo-icosahedron with mer stereochemistry to its FeII centers, shown encapsulating B12F122− [28]. We also have a flourishing line of enquiry into conjugated polymers that are held together by metal-ion templation – the

A new approach to ferrocene derived alkenes via copper-catalyzed olefination

• Vasily M. Muzalevskiy,
• Aleksei V. Shastin,
• Alexandra D. Demidovich,
• Namiq G. Shikhaliev,
• Abel M. Magerramov,
• Victor N. Khrustalev,
• Rustem D. Rakhimov,
• Sergey Z. Vatsadze and
• Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2015, 11, 2072–2078, doi:10.3762/bjoc.11.223

• current values of oxidation at the iron atom. These findings allow us to state that the synthesized molecules are promising starting materials for the electrochemical synthesis of ferrocene-containing conjugated polymers. Conclusion In conclusion, a novel stereoselective route to ferrocenyl haloalkenes

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

Synthesis and chemosensing properties of cinnoline-containing poly(arylene ethynylene)s

• Natalia A. Danilkina,
• Petr S. Vlasov,
• Semen M. Vodianik,
• Andrey A. Kruchinin,
• Yuri G. Vlasov and
• Irina A. Balova

Beilstein J. Org. Chem. 2015, 11, 373–384, doi:10.3762/bjoc.11.43

• type of response, conjugated polymers for sensing are termed as amplifying fluorescent polymers (AFPs) [4]. The mechanism of the response amplification can be explained in terms of the "molecular wire" concept [2][3][4][5][6][7][8][9]. Binding of a single analyte molecule to a single recognition site

• . Such materials find widespread use in sensing of metal ions and anions, detection of explosives and various biomolecules [2−4]. Among the great variety of known conjugated polymers, poly(arylene ethynylene)s (PAEs) are one of the most promising materials in the search for new chemical sensors [7]. A

• Optical sensors provide an efficient and sensitive approach for the rapid detection and identification of a wide range of chemical substrates by measuring the changes of optical properties such as absorbance, reflectance, luminescence, or fluorescence [1]. Among them a type of sensors based on conjugated

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

• Miriam Goll,
• Adrian Ruff,
• Erna Muks,
• Felix Goerigk,
• Beatrice Omiecienski,
• Ines Ruff,
• Rafael C. González-Cano,
• Juan T. Lopez Navarrete,
• M. Carmen Ruiz Delgado and
• Sabine Ludwigs

Beilstein J. Org. Chem. 2015, 11, 335–347, doi:10.3762/bjoc.11.39

• precursor monomers which give access to post-polymerization reactions. Ionic groups on conjugated polymers – so-called conjugated polyelectrolytes [25] – are discussed in the context of solubility tuning [26], sensor applications [27], improvement of solar cell performance by usage as hole injection layers

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

• 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

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

• the triads, theoretical DFT and TDDFT calculations were performed. Keywords: BODIPY; diketopyrrolopyrrole; organic semiconductors; organic solar cells; thiophene; Introduction The discovery of photoinduced electron transfer from conjugated polymers to fullerene (C60), and the favourable

• 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

• over conjugated polymers, such as (i) synthetic reproducibility, (ii) higher structural versatility, (iii) ease of purification by recrystallisation and/or chromatography and therefore monodispersity, (iv) higher degrees of crystallinity and (vi) the possibility of vacuum deposition or solution

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

• -conjugated polymers have attracted attention in the last years as promising active hole-transporting materials, which have a wide range of applications in electro-optical devices [1][2][3][4]. Polyfluorenes (PFs) are the most often investigated semiconducting polymers and are considered promising candidate

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

• of the molecular weight was demonstrated for the first time in flow for conjugated polymers by accurate addition of catalyst to the monomer solution. The P3HT samples synthesized in flow showed comparable performance to commercial P3HT samples in bulk heterojunction solar cell devices. Keywords

• : conjugated polymers; continuous-flow synthesis; controlled polymerization; flow chemistry; organic solar cell materials; Introduction Poly(3-hexylthiophene), P3HT, is the most investigated material in bulk heterojunction (BHJ) organic solar cells (OSC) [1]. The reasons for its dominance in the field include

• monomer-to-catalyst ratio with variations in reagent concentration and flow rates. This methodology enables the controlled synthesis of conjugated polymers in flow exclusively by the adjustment of the feed of monomer and initiator into the tube reactor. The major challenge in this study was to find

Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes

• Tsutomu Konno,
• Misato Kishi and
• Takashi Ishihara

Beilstein J. Org. Chem. 2012, 8, 2207–2213, doi:10.3762/bjoc.8.249

• ; carbometallation; diyne; enediyne; fluorine; highly regioselective; highly stereoselective; Introduction trans-Enediynes (trans-hex-3-ene-1,5-diynes), as shown in Figure 1, are well-recognized as one of the most important building blocks because they are frequently utilized for the synthesis of π-conjugated

• polymers, which have attracted much attention in the fields of electronic and photonic materials science [1][2][3]. While numerous synthetic approaches to non-fluorinated trans-enediynes have been reported so far, there has been quite a limited number studies on the preparation of fluoroalkylated trans

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

• materials with extended π-conjugation have attracted considerable attention in recent years as a new class of active organic materials for optoelectronic applications [1][2][3][4]. Among the conjugated polymers, a number of poly(9-alkylfluorene)s (PFs) and poly(9,9-dioctylfluorene) (PDOF) polymers in

• particular have been the focus of much research as encouraging candidates for organic light-emitting diodes (OLEDs) due to their pure blue luminescence and high efficiency [5][6][7][8][9][10]. The application of PFs and PDOF conjugated polymers is limited by unwanted side effects, such as aggregation and a

• interactions; bulky groups (also known as stoppers) are attached at the ends of the axle to prevent dethreading of the host. In the past few years many authors have demonstrated that the encapsulation of conjugated polymers into macrocycle cavities plays an important role in the construction of diverse

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

• -triazole co-oligomers were investigated by UV–vis spectroscopy and cyclic voltammetry. Several co-oligomers were electropolymerized to the corresponding conjugated polymers. Keywords: acetylene; azide; click chemistry; thiophene; triazole; Introduction Oligo- and polythiophenes are among the most

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

• ; photoluminescence; solar cell; Introduction A useful strategy in the design of new polymers for electronic applications is to incorporate chromophores which are highly absorbing and emitting in the visible and near infrared region into π-conjugated polymers chains. Potentially useful chromophores for electronic

• -interactions via molecular orbital overlapping and excition coupling effects [7][8][9], whilst electronic interactions and strong intermolecular forces lead to a high thermal stability of up to 500 °C. For chemical incorporation into conjugated polymers, the solubility of the DPP compound needs to be increased

• about 105 nm. Cyclovoltammetric studies indicated quasi-reversible oxidation and reduction behaviour, the band gap being about 2 eV. Characteristic properties of P-1 are listed in Table 1. In a comprehensive study, Zhu et al. prepared a number of highly luminescent DPP-based conjugated polymers [31

Synthesis of mesogenic phthalocyanine-C₆₀ donor–acceptor dyads designed for molecular heterojunction photovoltaic devices

• Yves Henri Geerts,
• Olivier Debever,
• Claire Amato and
• Sergey Sergeyev

Beilstein J. Org. Chem. 2009, 5, No. 49, doi:10.3762/bjoc.5.49

• , firstly in the pristine form and later as easily soluble derivatives such as phenylcyclopropa[6,6]C60-butanoic acid methyl ester (PCBM, 1, Figure 1) [9][10][11][12]. It has been used in a combination with a plethora of conjugated polymers [13][14][15][16][17][18] as well as small molecules [19][20][21

New diarylmethanofullerene derivatives and their properties for organic thin- film solar cells

• Daisuke Sukeguchi,
• Surya Prakash Singh,
• Mamidi Ramesh Reddy,
• Hideyuki Yoshiyama,
• Rakesh A. Afre,
• Yasuhiko Hayashi,
• Hiroki Inukai,
• Tetsuo Soga,
• Shuichi Nakamura,
• Norio Shibata and
• Takeshi Toru

Beilstein J. Org. Chem. 2009, 5, No. 7, doi:10.3762/bjoc.5.7

• heterojunction solar cells; fullerene derivatives; high open-circuit voltage; Introduction Bulk heterojunction photovoltaic cells consisting of thin-film composites of conjugated polymers (donors) and fullerene derivatives (acceptors) are promising candidates for inexpensive, renewable solar energy conversion