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

• -dependent density functional theory (TD-DFT) calculations (see the Supporting Information File 1 for details). The UV–vis data indicates that the degrees of π-delocalization for the TTFVs and DTF compounds are quite similar. This result is congruous with the fact that diphenyl-TTFVs generally prefer a

Trifluoromethyl-substituted tetrathiafulvalenes

• Olivier Jeannin,
• Frédéric Barrière and
• Marc Fourmigué

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

• trifluoromethyl-substituted TFF derivatives are lightly orange colored, while the ester and cyano TTFs are dark red compounds. In order to rationalize these evolutions, we have performed TD-DFT calculations on the model molecules TTF, TTF-CF3, TTF-CO2Me and TTF-CN. The results are shown in Figure 2 and collected

• initial geometry optimization calculations. Final geometries are given in Supporting Information File 1. Representation of frontier orbitals included in Figure 2 were generated with Molekel 4.3 [57]. TD-DFT calculations were performed at the B3LYP/6-311G** level of theory, on the previously converged

• optical transitions deduced from TD-DFT calculations (see Table 3). View of the 2ac molecule. Thermal ellipsoids are shown at the 50% probability level. View of the 2bc molecule. Thermal ellipsoids are shown at the 50% probability level. View of the two crystallographically independent 4bc molecules

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

• which has previously and incorrectly been described as an n→π* transition [16][20]; however, TD-DFT calculations predict this to be π→π* (Figure 3) [27][28]. The n→π* transition was calculated to have a slightly higher energy transition with an oscillator strength of 0; thus, it should not be visible in

Columnar/herringbone dual crystal packing of pyrenylsumanene and its photophysical properties

• Binod Babu Shrestha,
• Shuhei Higashibayashi and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2014, 10, 841–847, doi:10.3762/bjoc.10.80

• maximum of 1 was evidently red-shifted relative to those of 3 and pyrene. The 355 nm absorption band of 1 was assigned to the HOMO–LUMO transition by TD-DFT calculations (ωB97XD/6-31G(d)). DFT calculations also demonstrated that the HOMO and LUMO of 1 are primarily located on the pyrene moiety (Figure 4

Photoionisation of the tropyl radical

• Kathrin H. Fischer,
• Patrick Hemberger,
• Andras Bodi and
• Ingo Fischer

Beilstein J. Org. Chem. 2013, 9, 681–688, doi:10.3762/bjoc.9.77

• calculated the EOM-CCSD/cc-pVTZ excitation energies for the triplet states, using QChem 4 [44] at the DFT-optimised ground state tropyl ion geometry, to be 3.82 and 4.00 eV, corresponding to 10.05 and 10.23 eV photon energies. TD-DFT calculations yield 9.70, 10.05 eV (B3LYP/6-311++G(d,p)); 9.86, 10.25 (M06

• by a 1 eV gap to the next electronic excited state. EOM-CCSD vertical-excitation-energy calculations predict that the next higher lying state is a triplet at 12.48 eV followed by two more triplet states in ca. 100 meV intervals as well as several singlet states around 12.8 eV. TD-DFT calculations, on

Toward unidirectional switches: 2-(2-Hydroxyphenyl)pyridine and 2-(2-methoxyphenyl)pyridine derivatives as pH-triggered pivots

• Christina Tepper and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2012, 8, 977–985, doi:10.3762/bjoc.8.110

• (TD-DFT) with B3LYP as a functional and by employing the 6-31G* basis set (Figure 6b). TD-DFT calculations were performed at the optimized ground-state geometries of (M)-13 and (P)-13, calculating the energy, oscillator strength and rotatory strength for each of the 200 lowest singlet excitations. The

The arene–alkene photocycloaddition

• Ursula Streit and
• Christian G. Bochet

Beilstein J. Org. Chem. 2011, 7, 525–542, doi:10.3762/bjoc.7.61

• UV absorption band at 380 nm was observed. This absorption band fits well with TD-DFT calculations. He proposes that re-aromatization of this intermediate takes place via a zwitterionic species or through a proton catalyzed pathway. We recently found in our laboratories that the intramolecular

Predicting the UV–vis spectra of oxazine dyes

• Scott Fleming,
• Andrew Mills and
• Tell Tuttle

Beilstein J. Org. Chem. 2011, 7, 432–441, doi:10.3762/bjoc.7.56

• the basis for the single point excited state calculations. The six lowest singlet vertical excitation energies and oscillator strengths from the TD-DFT calculations were used to predict the UV–vis spectrum for each dye through the fitting of a Gaussian (with the GaussView default parameters for half

• , and in each case the magnitude is consistently 3–4 Debye. This is indicative of CT along the extended aromatic system and consistent with the classical description of these excitations. Performance of functionals and solvent models The TD-DFT calculations were carried out using the selection of

• spatial overlap between the orbitals involved in the excitation. Where more than one set of orbitals contribute to the excitation (as commonly occurs in TD-DFT calculations) the orbital overlaps are scaled by the contribution (κ) from each pair. In the following, we have employed the same form of Λ as

Syntheses and properties of thienyl-substituted dithienophenazines

• Annemarie Meyer,
• Eva Sigmund,
• Friedhelm Luppertz,
• Gregor Schnakenburg,
• Immanuel Gadaczek,
• Thomas Bredow,
• Stefan-S. Jester and
• Sigurd Höger

Beilstein J. Org. Chem. 2010, 6, 1180–1187, doi:10.3762/bjoc.6.135

• : oligothiophenes; phenazines; scanning tunneling microscopy; self-assembled monolayers; TD-DFT calculations; Introduction Thiophene based oligomers and polymers have drawn considerable interest as active materials in various fields of organic electronics such as organic light-emitting diodes (OLEDs), organic thin

• of the absorption and emission spectra. Spectral data of oligothiophenes in CH2Cl2.. Lowest vertical excitation energies obtained by B3LYP/TZVP TD-DFT calculations of the quaterthiophene 19 and derivatives as well as sexithiophene 20 and derivatives (gas phase and in CH2Cl2) in eV, and oscillator

An enantiomerically pure siderophore type ligand for the diastereoselective 1 : 1 complexation of lanthanide(III) ions

• Markus Albrecht,
• Olga Osetska,
• Thomas Abel,
• Gebhard Haberhauer and
• Eva Ziegler

Beilstein J. Org. Chem. 2009, 5, No. 78, doi:10.3762/bjoc.5.78

• functional and by employing the LANL2DZ basis set [37]. TD-DFT calculations were performed at the optimized ground-state geometry (B3LYP/LANL2DZ), calculating the energy, oscillator strength and rotatory strength for each of the 200 lowest singlet excitations. The CD spectrum was simulated by overlapping