Gary J. Balaich

Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene

The synthesis, structural, and electronic properties of nine 1,3-diphenyl-6-alkyl/aryl substituted pentafulvenes were studied. Pyrene ring π-π interactions were revealed from analysis of the experimental crystal packing of 1,3-diphenyl-6-(1-pyrene)fulvene and supporting DFT calculations. Photophysical properties derived from UV-vis and fluorescence emission measurements demonstrated tunable and low HOMO-LUMO band gaps for the series. The presented results point to a model synthetic approach for incorporation of extended π systems and donor-π-acceptor groups for fulvene-based electronic materials.

Symmetrical bis(fulvene) chromophores: model compounds for acceptor–donor–acceptor dye architectures

Four model bis(pentafulvene) chromophores have been prepared with a (fulvene)A–D–A(fulvene) architecture. Conjugation of the central donor group with the pendant fulvene rings was apparent from a single crystal X-ray study of the bis(pentafulvene) with 2,5-dihexyloxyphenyl as the central donor group. UV-Vis results indicated a tunable bandgap in the range of 400–700 nm by varying the nature of the central donor in this series of dyes.

New C2-symmetric cyclo­penta­diene dimer from sodium naphthalenide reduction of 1,3,6-tri-tert-butyl­fulvene

The sodium naphthalenide reduction of 1,3,6-tri-tert-butylxadfulvene gave the dimer, rac-3,4-bis(1,4-di-tertxadbutylxadcycloxadpenta-1,3-dien-2-yl)-2,2,5,5-tetraxadmethylxadhexane [C36H62, (II)] after protonation of the disodium salt of the bisxad(cycloxadpentaxaddienylxadethane) intermediate. Bond distances and angles for (II) are consistent with a bisxad(cycloxadpentaxaddiene) structure. The ansa bridge bond is long, at 1.592u2005(2)u2005A. The substitution pattern on the cycloxadpentaxaddiene rings, as well as the ansa bridge, result in an overall C2 symmetry for (II).

3-(4-Bromo-phen-yl)cyclo-pent-2-en-1-one.

In the title compound, C11H9BrO, the cyclopentenone ring is almost planar with an r.m.s. deviation of 0.0097u2005Å. The largest inter-ring torsion angles [2.4u2005(3), 1.3u2005(3) and 3.53u2005(2)°] reveal only a very small twist between the rings, and suggest that the two rings are conjugated. The molecule is slightly bowed, as shown by the small dihedral angle between the rings [5.3u2005(1)°]. The crystal packing pattern consists of parallel sheets that stack parallel to the ac plane. Each sheet consists of molecules that pack side-to-side with the same relative orientation of phenyl and cyclopentenone rings along the a- and c-axis directions. Slipped side-to-side, face-to-face and edge-to-face interactions exist between pairs of sheets with edge-to-edge and edge-to-face O⋯H—C(sp 2) weak hydrogen-bond contacts. A relatively short edge-to-face contact (2.77u2005Å) also exists between pairs of sheets.

(E)-1-[1-(3-Phenylcyclopenta-2,4-dien-1-ylidene)ethyl]pyrrolidine

The title compound, C17H19N, is a disubstituted pentaxadfulvene obtained from the hydroxadamination of 1-phenyl-3-trixadmethylxadsilylethynylxadcycloxadpentaxaddiene and has monoclinic P21/n symmetry at 100u2005K. C—H⋯π ring interxadactions between neighboring molxadecules consolidate the packing. To the authors knowledge, this reaction is the first reported example of a non-transition metal catalyzed hydroxadamination with concomitant desilylation.

1,3-Bis(4-bromo­phen­yl)propane

The title compound, C15H14Br2, obtained through the reduction of 4,4′-dixadbromoxadchalcone, has monoclinic P21 symmetry at 100u2005K. No directional interxadactions could be identified in the crystal.

9-(3,5-Di­methyl­benzyl­idene)-8-(3,5-di­methyl­phen­yl)-1,3,5,7-tetra­phenyl-2,4,7,8-tetra­hydro-4,7-methano­azulene aceto­nitrile disolvate

The title Diels–Alder product, C52H44·2CH3CN, was obtained in trace quxadantity as the `endo isomer during the synthesis of 1,3-diphenyl-6-(3,5-dixadmethylxadphenxadyl)fulvene. One of the two co-crystallized acetoxadnitrile molxadecules is linked to the main molxadecule by a weak C—H⋯N hydrogen bond.

Synthesis of reactive 1,3-diphenyl-6-aryl-substituted fulvene chromophores

This data article describes a detailed synthetic strategy and experimental data for the synthesis of brominated fulvene chromophores as reactive precursors/monomers for conjugated organic materials. Metal-mediated coupling reactions of brominated fulvenes would result in conjugated small molecules or polymers that would find application as organic light emitting diodes (OLEDs) and photovoltaic (PV) applications.

Crystal structure of chlorido­(dimethyl sulfoxide-κS)bis­[4-(pyridin-2-yl)benzaldehyde-κ3C2,N]iridium(III) aceto­nitrile monosolvate

The title iridium(III) complex crystallizes as a acetonitrile monosolvate and has the IrIII atom in a distorted octahedral coordination within a C2N2ClS coordination set.