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

• chelated with zinc(II) and BF2+ and the optical and electrochemical properties were studied. Fluorination had little effect on the optical properties of both the zinc(II) and BF2+ complexes, with λmax in solution around 755 nm and 785 nm, and high molar absorptivities of 100 × 103 M−1cm−1 and 50 × 103 M

• little effect on the optical properties of the BF2+ and zinc(II) chelates, and only had a small effect on the electrochemical properties, with the largest increase in oxidation and reduction potentials of 0.1 V observed for L1 and L4 chelates compared to WS3 chelates. Zinc(II) chelates of L1 and L4 are

• Figure 3. The fluorinated complexes had weight loss profiles similar to each other with a 5% loss between 438 °C and 474 °C, all lower than that of the unfluorinated Zn(WS3)2 at 517 °C. Optical properties Optical studies for the zinc(II) and BF2+ complexes were performed in chloroform solutions and with

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• well in solution. Complete characterization of both the intermediate and the final compounds was performed by 1H NMR, 13C NMR and mass spectrometry (see details in Supporting Information File 1). Optical properties Figure 1 presents the UV–vis absorption spectra of COOP-nHT-TBDTs 1–4 in solution and in

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

• ], however the subsequent different organization in the solid state might be the main factor responsible for the observed variation of the HOMO and LUMO energy levels, which is in perfect agreement with the different optical properties. Interestingly, the deep HOMO energies of both polymers would result in

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• -DPP2, under N2 atmosphere, was determined to be 378 and 380 °C, respectively, suggesting the high thermal stability for these compounds as donor materials. Optical properties The UV–vis absorption spectra of TTA-DPP4 and TTA-DPP2 in chloroform solutions and as-spun thin films are depicted in Figure 4

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

• Wei Li,
• Munechika Otsuka,
• Takehito Kato,
• Yang Wang,
• Takehiko Mori and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

• properties The UV–vis absorption spectra were employed to evaluate the optical properties of 3,6-Cbz-EDOT and 2,7-Cbz-EDOT. The spectra were measured in CH2Cl2 and in thin films (spin-coated on an ITO glass). The absorption maximum (λmax) of 3,6-Cbz-EDOT in CH2Cl2 was 362 nm, whereas the thin film showed the

Syntheses of dibenzo[d,d']benzo[2,1-b:3,4-b']difuran derivatives and their application to organic field-effect transistors

• Minh Anh Truong and
• Koji Nakano

Beilstein J. Org. Chem. 2016, 12, 805–812, doi:10.3762/bjoc.12.79

• quantum yield (Φ = 61% in CHCl3 solution). To investigate the structure–property relationship of DBBDFs and DNBDFs, the optical properties of syn-DBBDF 5 and syn-DNBDF 6 were compared with those of anti-DBBDF 3 and anti-DNBDF 4. The UV–vis spectra of anti-DBBDF 3 and anti-DNBDF 4 were reported to show

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• standard): Mn = 27900 g·mol−1, Mw/Mn = 1.83. 1H NMR spectrum of the polyrotaxane 3·TM-βCD copolymer in CDCl3. DSC traces on second heating scan of 3, 3·TM-βCD and 3·TM-γCD compounds. Optical properties of 3·TM-γCD (dotted line), 3·TM-βCD (dashed line) and 3 (solid line) polymers: absorption spectra at 10−1

2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties

• Yury A. Sayapin,
• Inna O. Tupaeva,
• Alexandra A. Kolodina,
• Eugeny A. Gusakov,
• Vitaly N. Komissarov,
• Igor V. Dorogan,
• Nadezhda I. Makarova,
• Anatoly V. Metelitsa,
• Valery V. Tkachev,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2015, 11, 2179–2188, doi:10.3762/bjoc.11.236

• -point energy correction (Etot + ZPE, а.u.) and relative energies (ΔE, kcal/mol) of the NH and OH tautomeric forms of compounds 5 and 6 calculated using the PBE0/6-311+G** method in the gas phase and in DMSO solution. Optical properties of 2-(2-alkoxycarbonyl-6-hydroxyphenyl)benzoxazoles 11a–f in heptane

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

• properties of 54 (n = 0–2) are shown in Table 4. The optical properties of 54 (n = 0–2) in solution (Table 4) follow a general trend of decreasing the absorption onset, while increasing the conjugation length. The electrochemistry of each H-shaped system 54 (n = 0–2) on the other hand is not so

• = 0–2) containing a central thieno[3,4-d][1,3]dithiole-2-one unit proceeded smoothly, with yields of 77% for n = 0, 82% for n = 1 and 39% for n = 2 (Scheme 14). The oligothiophene half-unit precursors, 55 (n = 0–2), were synthesised following synthetic pathway B. The electrochemical and optical

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• nanoobjects based on the self-assembly of TTFs were rapidly advanced, and a large number of functional properties such as electronic, magnetic, and optical properties were recently reported. Based on these developments of nanoscience, the construction of conducting nanoobjects has also been investigated to

New palladium–oxazoline complexes: Synthesis and evaluation of the optical properties and the catalytic power during the oxidation of textile dyes

• Rym Hassani,
• Mahjoub Jabli,
• Yakdhane Kacem,
• Jérôme Marrot,
• Damien Prim and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2015, 11, 1175–1186, doi:10.3762/bjoc.11.132

• %). The oxazolines were prepared from enantiomerically pure α-aminoalcohols. The structures of the synthesized palladium complexes were confirmed by NMR, FTIR, TOFMS, UV–visible spectroscopic analysis and X–ray diffraction. The optical properties of the complexes were evaluated by the determination of the

• determined. Keywords: aminoalcohols; catalysis; dye decolorization; optical properties; oxazolines; palladium complexes; Introduction Palladium complexes have been used as starting materials to prepare polymers [1], agrochemicals [2], pharmaceuticals [3], flavors and fragrances [4]. They have also been

• PdII ions, leading to the adsorption of dyes. Moreover, the decolorization of the solution by Pd and Pd complexes has also been applied [23]. In this paper, we report the synthesis and characterization of some new palladacycles. Optical properties were determined and the catalytic activity of these

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

• Rupert G. D. Taylor,
• Joseph Cameron,
• Iain A. Wright,
• Neil Thomson,
• Olena Avramchenko,
• Alexander L. Kanibolotsky,
• Anto R. Inigo,
• Tell Tuttle and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

• incomplete reaction of all the bromine atoms), and this is attributed to the increased solubility of the intermediates, which in turn increases their statistical likelihood of reacting further. Optical and electrochemical properties The optical properties of TTFs 1 and 2 were analysed by solution state UV

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

• Yoann Cotelle,
• Marie Hardouin-Lerouge,
• Stéphanie Legoupy,
• Olivier Alévêque,
• Eric Levillain and
• Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

• supports the graphical representation of the stepwise oxidation of molecular clips 1, 2 and 3 (Scheme 3). Optical and spectroelectrochemical properties The optical properties of oxidized states of molecular clip 1 were monitored by UV–vis–NIR spectroscopy, by successive aliquot addition of NOSbF6 (5 × 10−3

Discrete multiporphyrin pseudorotaxane assemblies from di- and tetravalent porphyrin building blocks

• Mirko Lohse,
• Larissa K. S. von Krbek,
• Sebastian Radunz,
• Suresh Moorthy,
• Christoph A. Schalley and
• Stefan Hecht

Beilstein J. Org. Chem. 2015, 11, 748–762, doi:10.3762/bjoc.11.85

• being a mere spacer and scaffold connecting the binding sites, porphyrins also offer interesting physical and optical properties [51][52]. Therefore, they have played a pivotal role in supramolecular chemistry [53][54][55][56][57][58][59][60][61][62][63][64][65][66], for example as potential candidates

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

• Mathieu L. Lepage,
• Antoine Mirloup,
• Manon Ripoll,
• Fabien Stauffert,
• Anne Bodlenner,
• Raymond Ziessel and
• Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

• state. In addition, they can be easily derivatized [31][32][33][34][35][36][37]. If the optical properties of BODIPY are very sensitive to modification of the pyrrole core [38][39], they are less sensitive to the substitution of the central pseudo meso position [40][41]. Additionally, the fluorine

Trifluoromethyl-substituted tetrathiafulvalenes

• Olivier Jeannin,
• Frédéric Barrière and
• Marc Fourmigué

Beilstein J. Org. Chem. 2015, 11, 647–658, doi:10.3762/bjoc.11.73

• derivatives described here is shown in Figure 1 and demonstrates that the trifluoromethyl group anodic shift observed in the order CO2Me < CF3 < CN correlate well with the σmeta Hammet constant. Optical properties The evolution of the lowest energy absorption bands is also reported for the different TTF

• introduced on the dithiole ring upon substitution with the CN and CO2Me (−M) EWG are not offset by the competing CF3 group, confirming its much weaker mesomeric effect on the conjugated dithiole core. Optical properties and theoretical calculations have shown that the HOMO–LUMO gap is not much modified in

Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation

• Martin Weiser,
• Sergej Hermann,
• Alexander Penner and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2015, 11, 568–575, doi:10.3762/bjoc.11.62

• photocatalytic process was used also for intramolecular additions. For the oxidative mode towards the anti-Markovnikov-type regioselectivety, PDI was a highly suitable photocatalyst based on its electrochemical and optical properties. Photocatalytic additions of a variety of alcohols to styrene derivatives gave

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

• 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

• connects head-to-tail oriented cinnoline units (orange–purple) the additional splitting was observed (for zoom copies of NMR spectra see Supporting Information File 2). Optical properties and metal-sensing ability of cinnoline-containing PAEs The absorption spectrum in the UV–vis range of THF solutions of

• the cinnoline ring means that the conjugation extension in the repeating unit that comes from the triple bond is more important for the collective quenching effect than the degree of polymerization. In order to prove that the observed changes in optical properties of PAEs 10a,b were induced by Pd2

IR and electrochemical synthesis and characterization of thin films of PEDOT grown on platinum single crystal electrodes in [EMMIM]Tf₂N ionic liquid

• Andrea P. Sandoval,
• Marco F. Suárez-Herrera and
• Juan M. Feliu

Beilstein J. Org. Chem. 2015, 11, 348–357, doi:10.3762/bjoc.11.40

• reaction of PEDOT were studied using in situ FTIR spectroscopy. Keywords: AFM; [EMMIM]Tf2N ionic liquid; in situ IR; PEDOT; Pt single crystals; Introduction Conducting polymers have been subject of an intense research during the last decades because they exhibit high conductivity and interesting optical

• properties. These properties allow their use in several electronic devices [1][2]. The poly(3,4-ethylenedioxythiophene) (PEDOT) is one of the most conducting and stable (thermal and chemical) conducting polymer. For these reasons PEDOT thin films have been extensively studied [3]. Special attention has been

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

• broad spectral shapes with maxima around 530 nm. From the spectra of the neutral compounds a clear distinction between the copolymer and the blend is not possible. Monitoring the optical properties during the electrochemical oxidation process by in situ spectroelectrochemistry, however, gives further

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• fluorescence change in the complex with DNA, while two amino groups in 3,8-position result in a weak fluorescence with strong emission increase upon DNA binding [52][53][56]. A pronounced influence of the substituent at phenanthridine position 6 on the optical properties of the chromophore also had significant

Synthesis and properties of novel star-shaped oligofluorene conjugated systems with BODIPY cores

• Clara Orofino-Pena,
• Diego Cortizo-Lacalle,
• Joseph Cameron,
• Muhammad T. Sajjad,
• Pavlos P. Manousiadis,
• Neil J. Findlay,
• Alexander L. Kanibolotsky,
• Dimali Amarasinghe,
• Peter J. Skabara,
• Tell Tuttle,
• Graham A. Turnbull and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2704–2714, doi:10.3762/bjoc.10.285

• molecular bromine which was used previously [33]. Thermal, electrochemical and optical properties TGA and DSC analyses All of the final target compounds showed good thermal stability. Thermogravimetric analysis (TGA) revealed decomposition temperatures in the range 396–442 °C (Table 1, Figure S1, Supporting

• levels for both families are similar, whereas, in general, the LUMO levels of the Y-Bn family are lower, leading to narrower electrochemical HOMO–LUMO gaps. Optical properties The optical properties of the oligomers were studied in dichloromethane solutions. An image of toluene solutions of both families

• under ambient conditions and UV-illumination is presented in Figure 2. The effect of the substitution pattern of the BODIPY core with fluorene arms (either at the α- or β-positions) on the optical properties of the materials can be observed with the naked eye. The compounds of the Y-Bn (n = 1–4) series

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

• . Electrochemical and optical properties The oxidation and reduction processes of 9 and 10 in solution are shown in Figure 2 and Table 1 summarises the corresponding electrochemical data. Upon oxidation, 9 shows two reversible peaks at +0.42 and +0.73 V and 10 shows three reversible processes at +0.37, +0.57 and

• expected to obtain a lower HOMO–LUMO energy gap value for 10. On the contrary, compound 9 displays a slightly lower energy gap both in solution and in the solid state. This difference is unusual for a system with extended conjugation and is addressed later. The optical properties of compounds 9 and 10 were

Host–guest-driven color change in water: influence of cyclodextrin on the structure of a copper complex of poly((4-hydroxy-3-(pyridin-3-yldiazenyl)phenethyl)methacrylamide-co-dimethylacrylamide)

• Nils Retzmann,
• Gero Maatz and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 2480–2483, doi:10.3762/bjoc.10.259

• studied extensively, causing for example a blue to red color transition of polydiacetylenes (PDAS) due to the formation of inclusion complexes [6][7]. Azo dyes, with their remarkable ability to form stable azo–metal chelate complexes with outstanding thermal and optical properties have been studied widely

Synthesis and optical properties of pyrrolidinyl peptide nucleic acid carrying a clicked Nile red label

• Nattawut Yotapan,
• Chayan Charoenpakdee,
• Pawinee Wathanathavorn,
• Boonsong Ditmangklo,
• Hans-Achim Wagenknecht and
• Tirayut Vilaivan

Beilstein J. Org. Chem. 2014, 10, 2166–2174, doi:10.3762/bjoc.10.224

• , pyrrolidinyl peptide nucleic acid (acpcPNA) was labeled at its backbone with Nile red, a solvatochromic benzophenoxazine dye, by means of click chemistry. The optical properties of the Nile red-labeled acpcPNA were investigated by UV–vis and fluorescence spectroscopy in the absence and in the presence of DNA

• . Melting temperature data and optical properties of the Nile red-labeled acpcPNAs and their hybrids with various DNA are summarized in Table 2. Thermal denaturation experiments suggest that the Nile red-labeled acpcPNA 10mer-Nr can form a stable hybrid with complementary DNA. In contrast to some other

• addition of cyclodextrin, which indicates possible interactions between the groove-bound Nile red and cyclodextrin. To better understand the effect of neighboring bases on the optical properties of the Nile red-labeled acpcPNA and its duplexes with DNA, four Nile red-labeled acpcPNA sequences (11merAA-Nr