Tuning the size of a redox-active tetrathiafulvalene-based self-assembled ring

• Sébastien Bivaud,
• Sébastien Goeb,
• Vincent Croué,
• Magali Allain,
• Flavia Pop and
• Marc Sallé

Beilstein J. Org. Chem. 2015, 11, 966–971, doi:10.3762/bjoc.11.108

• M6L3 cavity in which the curvature of the exTTF is closer to ligand L1. The new M6L3 system has been fully characterized and exhibits electrochemical properties which are essentially similar to those of M4L2, indicating that the strong π-donating ability of the cavity can be maintained while enlarging

Carboxylated dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, electronic properties, and complexation with zinc ions

• Yunfei Wang and
• Yuming Zhao

Beilstein J. Org. Chem. 2015, 11, 957–965, doi:10.3762/bjoc.11.107

• considerably improved thermal stability, a property particularly beneficial for practical device and material applications. Conclusion In summary, we have synthesized carboxylated diphenyl-TTFV 6 and phenyl-DTF 7 as redox-active ligands to complex with Zn(II) ions. The electronic and electrochemical properties

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

• Sandrina Oliveira,
• Dulce Belo,
• Isabel C. Santos,
• Sandra Rabaça and
• Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 951–956, doi:10.3762/bjoc.11.106

• S–S, C–N, S–H, N–H (S2–S3; N1–C1; N1–H1A; S2–H9; S5–H10; S6–H10). Short-contact details are given in Table S1 in Supporting Information File 1. Molecules in neighbouring stacks along a are tilted by 54.35° (Figure 3). Spectroscopic and electrochemical properties The electronic properties of 3 were

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

• Huixin Jiang,
• Virginia Mazzanti,
• Christian R. Parker,
• Søren Lindbæk Broman,
• Jens Heide Wallberg,
• Karol Lušpai,
• Adam Brincko,
• Henrik G. Kjaergaard,
• Anders Kadziola,
• Peter Rapta,
• Ole Hammerich and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104

• -TTF molecules and their electrochemical properties have previously been reviewed [1][2][3]. Here we make a brief discussion of some selected structures of relevance to those studied in this work, as shown in Figure 5. For the directly linked compound 15 [20] and the aryl/heteroaryl mono-bridged

Tuning of tetrathiafulvalene properties: versatile synthesis of N-arylated monopyrrolotetrathiafulvalenes via Ullmann-type coupling reactions

• Vladimir A. Azov,
• Diana Janott,
• Dirk Schlüter and
• Matthias Zeller

Beilstein J. Org. Chem. 2015, 11, 860–868, doi:10.3762/bjoc.11.96

• -type coupling reaction was employed for the preparation of several N-arylated monopyrrolotetrathiafulvalenes with variable substitution patterns. Spectroscopic and electrochemical properties of the coupling products strongly depend on the electronic nature of the aromatic substituents due to their

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

• (Shanghai, China). Tetrahydrofuran (THF) and acetonitrile (CH3CN) were distilled over CaH2 and stored under N2 atomsphere. Compounds 1–7 were synthesized by following our previous reports [37][38]. The electrochemical properties of 1–7 were recorded on a RST 5000 electrochemical workstation at a scan rate

Trifluoromethyl-substituted tetrathiafulvalenes

• Olivier Jeannin,
• Frédéric Barrière and
• Marc Fourmigué

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

• molecules. The preparation of the two positional isomers of bis(trifluoromethyl)-bis(carboxymethyl)tetrathiafulvalene 3bc and 4bc is also reported. The evolutions of (i) the geometry of the dithiole ring bearing the EWG, (ii) the electrochemical properties, (iii) the optical absorption (UV–vis) properties

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

• -ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-mtdt, 2), were synthesized and characterized. The electrochemical properties of these electronic donors were studied by cyclic voltammetry (CV) in dichloromethane. Both compounds show two quasi-reversible oxidation processes, versus Ag

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

• paid to the use of electrochemical methods to synthesize conducting polymers due to the high degree of control afforded during the polymerization reaction. On the other hand, thin films of conducting polymers are more suitable to explore electrochemical properties such as stability, capacitance

• electrochemical properties, as the ionic resistance or the electrocatalytic activity, of PEDOT are affected by the surface energy state of the electrode [6]. For example, it was found that the ionic resistance of the PEDOT films electrochemically synthesized on platinum electrodes increases in the order Pt(100

• electrochemical synthesis of PEDOT. The electrochemical properties of thin films of PEDOT are subsequently studied and compared with the behavior obtained in acetonitrile. Results and Discussion Cyclic voltammetry Figure 1 shows the cyclic voltammograms of EDOT in [EMMIM]Tf2N. The onset of the EDOT oxidation

An improved procedure for the preparation of Ru(bpz)₃(PF₆)₂ via a high-yielding synthesis of 2,2’-bipyrazine

• Danielle M. Schultz,
• James W. Sawicki and
• Tehshik P. Yoon

Beilstein J. Org. Chem. 2015, 11, 61–65, doi:10.3762/bjoc.11.9

• -absorbing photocatalysts for synthetic applications. Among the most attractive features of this approach is the availability of many known complexes with well-characterized photophysical and electrochemical properties. In particular, Ru(bpz)32+ is a powerful photooxidant that has proven to be uniquely

• of odd-electron intermediates such as radicals and radical ions under exceptionally mild reaction conditions. A large number of transition metal chromophores with well-characterized photophysical and electrochemical properties are known, and the influence of ligand modification on the photoredox

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

• generally increased with increasing molecular weight. This trend was most pronounced for Y-Bn (n = 1–4) and not so significant for the T-Bn (n = 1–4) series. In the latter case the Tg reached a saturation value at 99 °C for terfluorene T-B3. Electrochemistry The electrochemical properties of the materials

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

• Meriem Smadhi,
• Sophie de Bentzmann,
• Anne Imberty,
• Marc Gingras,
• Raoudha Abderrahim and
• Peter G. Goekjian

Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

• electrochemical properties [34] (Figure 1). They were also highly potent lectin aggregators. Among other aromatic glycoasterisks, Roy et al. described the synthesis of densely substituted hexaphenylbenzene glycoclusters [35]. In this work, we have designed a new family of low-valent glycoclusters based on a

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

• representative selection of pentacenes. Electrochemical properties of 3a–k compared to TIPSPc and 2a–c.a Supporting Information Supporting Information File 506: Experimental procedures and characterization data for all new compounds. Copies of 1H and 13C NMR, UV–vis, and emission spectra; CV, DSC, and TGA scans

Novel indolin-2-one-substituted methanofullerenes bearing long n-alkyl chains: synthesis and application in bulk-heterojunction solar cells

• Irina P. Romanova,
• Andrei V. Bogdanov,
• Inessa A. Izdelieva,
• Vasily A. Trukhanov,
• Gulnara R. Shaikhutdinova,
• Dmitry G. Yakhvarov,
• Shamil K. Latypov,
• Vladimir F. Mironov,
• Vladimir A. Dyakov,
• Ilya V. Golovnin,
• Dmitry Yu. Paraschuk and
• Oleg G. Sinyashin

Beilstein J. Org. Chem. 2014, 10, 1121–1128, doi:10.3762/bjoc.10.111

• methanofullerenes (AIMs) is described. Optical absorption, electrochemical properties and solubility of AIMs were studied. Poly(3-hexylthiophene-2,5-diyl) (P3HT)/AIMs solar cells were fabricated and the effect of the AIM alkyl chain length and the P3HT:AIM ratio on the solar cell performance was studied. The power

• of long-chain alkyl fragments to the IM nitrogen atom. As a result, the series of novel alkyl-containing indolin-2-one-substituted methanofullerenes (AIMs 2–9) were synthesized. Optical absorption and electrochemical properties of AIMs 1–9 were studied. Bulk heterojunction polymer solar cells based

• fullerene. UV–vis, IR, and NMR spectroscopy confirmed their structure. The composition was established by MALDI–TOF mass spectrometry. Optical absorption, electrochemical properties and solubility of AIMs Figure 2 compares a typical optical absorption spectrum of AIMs with those of PCBM and pristine

The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads

• Sarah Bay,
• Gamall Makhloufi,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 1006–1016, doi:10.3762/bjoc.10.100

• carbazole moieties as donors, and comprehensive physical organic studies of electronic and electrochemical properties investigated by steady state UV–vis and fluorescence spectroscopy as well as cyclic voltammetry. The obtained data are interpreted in the light of the Weller approximation to estimate the

AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds

• Qiuping Ding,
• Dan Wang,
• Puying Luo,
• Meiling Liu,
• Shouzhi Pu and
• Liyun Zhou

Beilstein J. Org. Chem. 2013, 9, 1949–1956, doi:10.3762/bjoc.9.231

• electrochemical properties [7][8][9][10][11][12][13][14][15]. Over the past decade, there has been growing interest in the development of new methods for the construction of isoquinoline. For instance, Yamamoto [16][17][18][19], Larock [20][21][22][23][24][25][26][27], and Wu [28][29][30][31][32][33][34][35] have

Incorporation of perfluorohexyl-functionalised thiophenes into oligofluorene-truxenes: synthesis and physical properties

• Neil Thomson,
• Alexander L. Kanibolotsky,
• Joseph Cameron,
• Tell Tuttle,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2013, 9, 1243–1251, doi:10.3762/bjoc.9.141

• containing perfluorohexylthiophene units at the terminal positions on the arms were synthesised, and their optical and electrochemical properties were investigated to determine the effect that the perfluorohexylthiophene unit has on the HOMO and LUMO properties of the oligomers. By synthesising a molecule

• and electrochemical properties by introducing perfluorohexylthiophene units at the terminal positions of the oligofluorene arms. Planarity of the backbone is an important concept in conjugated organic oligomers and polymers, as any twist in the dihedral angle between aromatic repeat units can lessen

• molecules that are structural isomers were synthesised and studied to compare the optical and electrochemical properties. Furthermore, a significantly larger molecule was synthesised to observe how a molecule with longer conjugated arms would also be affected by the perfluorohexylthiophene units. Results

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

• , fluorescence and quantum yield data for the ligands and complexes in acetonitrile solution. Electrochemical properties of dendrons and dendrimers a. Acknowledgements The authors would like to acknowledge the Alexander von Humboldt foundation (grant for AM).

Spectroscopic characterization of photoaccumulated radical anions: a litmus test to evaluate the efficiency of photoinduced electron transfer (PET) processes

• Maurizio Fagnoni,
• Stefano Protti,
• Davide Ravelli and
• Angelo Albini

Beilstein J. Org. Chem. 2013, 9, 800–808, doi:10.3762/bjoc.9.91

• deoxygenated solutions, except where otherwise noted. The examined solutions were irradiated on an optical bench equipped with a 150 W high-pressure mercury lamp, (λIRR = 313 nm). The electrochemical properties of TCB [8][9], DCN [8][9], DCA [8][9], DCP [10], DCP-ME [10], ME [45], PME [28], Et3N [60], iPr3N

Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors

• Francesca Pertici,
• Norbert Varga,
• Arnoud van Duijn,
• Matias Rey-Carrizo,
• Anna Bernardi and
• Roland J. Pieters

Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25

• units the phenylene-ethynylene unit has seen considerable interest in sensor [16] and molecular-electronics applications [17]. This is due to the specific fluorescent, conducting and electrochemical properties that the conjugated system confers to the molecule [18]. In the study of carbohydrate–protein

New enzymatically polymerized copolymers from 4-tert-butylphenol and 4-ferrocenylphenol and their modification and inclusion complexes with β-cyclodextrin

• Adam Mondrzyk,
• Beate Mondrzik,
• Sabrina Gingter and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2118–2123, doi:10.3762/bjoc.8.238

• several studies, especially with regard to its electrochemical properties. After electrochemical oxidation of the Fe(II) ion to Fe(III) a one-electron transfer from the phenol moiety takes place, in which a proton is transferred simultaneously [20]. Furthermore, 4-ferrocenylphenol shows an antianemic

Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups

• H. Bauke Albada,
• Alina-Iulia Chiriac,
• Michaela Wenzel,
• Maya Penkova,
• Julia E. Bandow,
• Hans-Georg Sahl and
• Nils Metzler-Nolte

Beilstein J. Org. Chem. 2012, 8, 1753–1764, doi:10.3762/bjoc.8.200

• dimensions and very different physicochemical and electrochemical properties. Firstly, ferrocene derivatives have redox potentials that are within the realm of biological systems, but ruthenocene derivatives do not [41]. Secondly, while most ferrocene derivatives exhibit a reversible one-electron oxidation

The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety

• Renjie Wang,
• Shouzhi Pu,
• Gang Liu and
• Shiqiang Cui

Beilstein J. Org. Chem. 2012, 8, 1018–1026, doi:10.3762/bjoc.8.114

• or ortho position of the terminal benzene ring were synthesized. Their photochromism, fluorescent-switch, and electrochemical properties were investigated. Among these diarylethenes, the one with a formyl group at the ortho position of benzene displayed the largest molar absorption coefficients and

• for the fluorescence photoswitching material. Electrochemical properties of diarylethenes 1–3 The electrochemical behaviors of diarylethene derivatives have attracted much attention because of their potential applications in molecular-scale electronic switches [57][58][59][60][61][62]. The

• electrochemical properties of 1–3 were evaluated by cyclic voltammetry (CV) under the same experimental conditions reported previously [13]. The CV curves of diarylethenes 1–3 are shown in Figure 7. The onset potentials (Eonset) of oxidation and reduction for 1o were initiated at +1.79 and −0.89 V, and those of

Hybrid super electron donors – preparation and reactivity

• Jean Garnier,
• Douglas W. Thomson,
• Shengze Zhou,
• Phillip I. Jolly,
• Leonard E. A. Berlouis and
• John A. Murphy

Beilstein J. Org. Chem. 2012, 8, 994–1002, doi:10.3762/bjoc.8.112

• ][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. Among the tetraazaalkenes, those that are converted to aromatic molecules upon oxidation, e.g., tetraazafulvalenes 1 and 2, are extremely reactive, and their electrochemical properties have been studied in some depth [13][14

• organic electron donors incorporating a "stronger" donor component and a "weaker" component, e.g., 9 or 10 would be prime candidates, as the driving force for the loss of their first electron should exceed that for the loss of their second. The electrochemical properties of some hybrid imidazolium

Self-assembly of Ru₄ and Ru₈ assemblies by coordination using organometallic Ru(II)₂ precursors: Synthesis, characterization and properties

• Sankarasekaran Shanmugaraju,
• Dipak Samanta and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2012, 8, 313–322, doi:10.3762/bjoc.8.34

• tetranuclear rectangular geometry with the dimensions of 5.53 Å × 12.39 Å. Furthermore, the photo- and electrochemical properties of these newly synthesized assemblies have been studied by using UV–vis absorption and cyclic voltammetry analysis. Keywords: cages; macrocycles; ruthenium(II); self-assembly; self

• novel, nanoscopic and functional metallamacrocycles and also to the study of their functional properties [15]. The photo- and electrochemical properties of our newly synthesized macrocycles (2a and 2b) are studied by UV–vis absorption and cyclic voltammetry investigations and the obtained results are