Single-molecule conductance of a chemically modified, π-extended tetrathiafulvalene and its charge-transfer complex with F₄TCNQ

• Raúl García,
• M. Ángeles Herranz,
• Edmund Leary,
• M. Teresa González,
• Gabino Rubio Bollinger,
• Marius Bürkle,
• Linda A. Zotti,
• Yoshihiro Asai,
• Fabian Pauly,
• Juan Carlos Cuevas,
• Nicolás Agraït and
• Nazario Martín

Beilstein J. Org. Chem. 2015, 11, 1068–1078, doi:10.3762/bjoc.11.120

• . Synthetic route to the target exTTF-based molecular wire 5. Kohn–Sham HOMO and LUMO, ionization potential (IP), electron affinity (EA) and image charge correction for occupied Δocc and Δvirt unoccupied orbitals. All quantities are in eV. Supporting Information Supporting Information File 150: Detailed

• , while the LUMO and all other unoccupied orbital levels were shifted by Σvirt=−EA − εL +Δvirt. Here, Δocc (Δvirt) is the image charge correction for the occupied (unoccupied) states, εH (εL) is the Kohn–Sham energy of the gas phase HOMO (LUMO), and IP(EA) is the gas phase ionization potential (electron

• affinity). All quantities are reported in Table 1 for both binding geometries. The alignment of the Breit–Wigner resonances related to both the HOMO and LUMO (at approximately −1 and 2.7 eV from the Fermi level, respectively) do not show a strong dependence on the binding geometry (Figure 9). The electron

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

• charge at the heterocyclic nitrogen N-5, and strong electron affinity and polar groups at the 3 and/or 8 position of the phenanthridine can efficiently and predictably regulate the spectroscopic response (UV–vis and fluorescence) of the chromophore [48]. The understanding of the intercalation process

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

• is consistent with DFT calculations (vide infra), showing in this case localisation of the LUMO exclusively on the BODIPY core. The positive inductive effect of four methyl groups attached to the core can also contribute to a decrease in the electron affinity of the BODIPY unit in this case. The HOMO

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

• Bradley D. Rose,
• Peter J. Santa Maria,
• Aaron G. Fix,
• Chris L. Vonnegut,
• Lev N. Zakharov,
• Sean R. Parkin and
• Michael M. Haley

Beilstein J. Org. Chem. 2014, 10, 2122–2130, doi:10.3762/bjoc.10.219

• . This modest alteration imparts an inherent propensity of the IF scaffold to be electron accepting [10][11]. A simple explanation for the high electron affinity of the IF is that to make all five rings formally aromatic two electrons must be added to the system, effectively creating two cyclopentadiene

• anions [12]. The result of the IFs high electron affinity is nearly balanced ambipolar charge transport in OFETs [11][13]. The synthetic precursors to 1, the indeno[1,2-b]fluorene-6,12-diones (IF-diones, 2, Figure 1) have also been explored as an active layer in OFETs. The first reported IF-dione OFET

Supercritical carbon dioxide: a solvent like no other

• Jocelyn Peach and
• Julian Eastoe

Beilstein J. Org. Chem. 2014, 10, 1878–1895, doi:10.3762/bjoc.10.196

• [43][48]. Solubility Surfactants Surfactant tails – fluorinated surfactants: Fluorine has a high electron affinity and electronegativity, hence fluorocarbons with a carbon number (n) that is equal to or greater than 4 have lower boiling points and refractive indices than the corresponding hydrocarbons

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

• Anastasia S. Kostyuchenko,
• Vyacheslav L.Yurpalov,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2014, 10, 1596–1602, doi:10.3762/bjoc.10.165

• by consequence their electron affinity (EA) and ionization potential (IP) are not appropriate [2]. Since these two parameters determine the redox, spectroscopic, electronic and optoelectronic properties of oligothiophenes, their tuning is of crucial importance in any design of new organic

cis–trans Isomerization of silybins A and B

• Michaela Novotná,
• Radek Gažák,
• David Biedermann,
• Florent Di Meo,
• Petr Marhol,
• Marek Kuzma,
• Lucie Bednárová,
• Kateřina Fuksová,
• Patrick Trouillas and
• Vladimír Křen

Beilstein J. Org. Chem. 2014, 10, 1047–1063, doi:10.3762/bjoc.10.105

• ) principle. According to this theory, hard acids react with hard bases whereas soft acids react with soft bases. The hardness is given by where I and A are the adiabatic ionization potential and the adiabatic electron affinity, respectively. The hardness of silybin B was not calculated, as the

Thermodynamically stable [4 + 2] cycloadducts of lanthanum-encapsulated endohedral metallofullerenes

• Yuta Takano,
• Yuki Nagashima,
• M. Ángeles Herranz,
• Nazario Martín and
• Takeshi Akasaka

Beilstein J. Org. Chem. 2014, 10, 714–721, doi:10.3762/bjoc.10.65

• fullerenes simultaneously possess a low ionizing potential and a high electron affinity [1][2]. For mono-La endohedral fullerenes such as La@C82, the electron transfer results in paramagnetism of the fullerene cage [5]. The di-La endohedral fullerenes such as La2@C80 show diamagnetism [6]. This feature leads

Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: a new molecular probe for ZnO nanoparticles with unusual fluorescence features

• Laura Bekere,
• David Gachet,
• Vladimir Lokshin,
• Wladimir Marine and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2013, 9, 1311–1318, doi:10.3762/bjoc.9.147

• electron donating and accepting properties of this molecule. The geometry was optimized by using the semiempirical AM1 method and the electronic spectra were calculated by using the TD B3LYP/6-31G(d,p) method. The ionization potential (IP) and electron affinity (EA) were calculated at the B3LYP/6-31G(d,p

A study on electrospray mass spectrometry of fullerenol C₆₀(OH)₂₄

• Mihaela Silion,
• Andrei Dascalu,
• Mariana Pinteala,
• Bogdan C. Simionescu and
• Cezar Ungurenasu

Beilstein J. Org. Chem. 2013, 9, 1285–1295, doi:10.3762/bjoc.9.145

• redistribution of odd electrons of fullerenyl radical anion, accounting for the formation of a final molecular anion [2M − 48OH + 2e]2− as observed at m/z 720 and depicted in Scheme 2. Taking into account the moderate electron affinity of fullerenols [32][33] and the fact that earlier extensive studies focused

Sexithiophenes as efficient luminescence quenchers of quantum dots

• Christopher R. Mason,
• Yang Li,
• Paul O’Brien,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202

• potential role in a range of device architectures [15][16]. Additionally, the formation of blends of conjugated oligomers and quantum dots can lead to attractive properties, taking advantage of facile charge transfer due to the high electron affinity of the quantum dot nanoparticles [17][18], as well as

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

• fastness, deep colour, luminescence with large Stokes-shifts, and a brilliant red colour enabling technical applications in colouring of fibers, plastics and surface coatings such as prints or inks. The electron-withdrawing effect of the lactam units causes the chromophore to have a high electron affinity

• the electron affinity, and phenothiazine significantly enhanced the hole injection ability. ThiophenylDPP-based copolymers The replacement of the phenyl groups in 3,6-diphenyl-substituted DPP derivatives by thiophenyl groups resulted in 3,6-(2-thiophenyl)-substituted DPP derivatives (thiophenylDPPs

Prediction of reduction potentials from calculated electron affinities for metal-salen compounds

• Sarah B. Bateni,
• Kellie R. England,
• Anthony T. Galatti,
• Handeep Kaur,
• Victor A. Mendiola,
• Alexander R. Mitchell,
• Michael H. Vu,
• Benjamin F. Gherman and
• James A. Miranda

Beilstein J. Org. Chem. 2009, 5, No. 82, doi:10.3762/bjoc.5.82

• could be used to predict the reduction potentials of a variety of metal-salen compounds, an important class of coordination compounds used in synthetic organic electrochemistry as electrocatalysts. Keywords: density functional theory; electron affinity; metal-salen; reduction potential; Introduction

• non-metal atoms. Vibrational frequencies were computed for each optimized geometry in order to verify them as stationary points and to obtain zero-point energies and thermal enthalpy corrections, such that enthalpies at 25 °C could be obtained. The electron affinity (EA) for a given metal-salen was

• grade dimethylformamide/0.1 M Bu4N+ BF4− versus Ag/0.1 M AgCl on a Bioanalytical Systems 50-W Voltammetric Analyzer. The potential of the reference electrode was +0.047 V versus SCE. Training set of 19 metal-salens. Correlation between electron affinity (EA) and Hammett σp parameter in the training set