196505-83-6Relevant articles and documents
Heterosuperbenzenes: A new family of nitrogen-functionalized, graphitic molecules
Draper, Sylvia M.,Gregg, Daniel J.,Madathil, Rethi
, p. 3486 - 3487 (2002)
A versatile synthetic route has been demonstrated to provide a series of soluble, fused polyaromatic C,N-molecules, with tunable optical and electronic properties and ligand functionality. The N-functionalized heterosuperbenzene, 1, is the founding member
Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry
Meitinger, Nicolas,Mengele, Alexander K.,Witas, Kamil,Kupfer, Stephan,Rau, Sven,Nauroozi, Djawed
, p. 6555 - 6562 (2020/10/02)
The synthesis of a series of tetraaryl cyclopentadienones comprising different substitution patterns is reported. Their photophysical and electrochemical properties are investigated by UV/Vis spectroscopy and cyclic voltammetry as well as by supporting quantum chemical simulations and reveal a distinct effect of substituents on the redox behavior of the molecules as well as the absorption properties of this class of compounds. While electrochemical data display a shift in reduction potential of up to 200 mV between the differently substituted cyclopentadienones, their photophysical investigations in differently polar solvents suggest a negative solvatochromic effect, although protic solvents induce a bathochromic shift. Crystal structure analyses of some derivatives confirm similarity with related cyclopentadienones while providing insight into intermolecular C–H···O and C–H···π interactions in the solid state.
Electronic Communication across Porphyrin Hexabenzocoronene Isomers
Martin, Max M.,Lungerich, Dominik,Haines, Philipp,Hampel, Frank,Jux, Norbert
supporting information, p. 8932 - 8937 (2019/05/29)
Single-molecule electronic components (SMECs) are envisioned as next-generation building blocks in quantum circuit systems. However, challenges such as the reproducibility of the electrode attachment to the individual molecules hamper their fundamental in
Superbenzene-Porphyrin Conjugates
Lungerich, Dominik,Hitzenberger, Jakob F.,Marcia, Mario,Hampel, Frank,Drewello, Thomas,Jux, Norbert
supporting information, p. 12231 - 12235 (2016/02/23)
A free-base porphyrin carrying two hexabenzocoronene (HBC) substituents in a trans arrangement and its zinc complex have been prepared. The compounds were characterized extensively and found to form tricationic dimers in the gas phase. X-ray crystallography confirms for the zinc complex a profound π-stacking of the HBC moieties. In contrast, the free-base porphyrin incarcerates n-heptane which essentially prevents π-stacking. Upon excitation of the HBC substituents, efficient energy transfer to the central porphyrin is observed. Super size me! The first porphyrin conjugate with two superbenzene units shows properties induced by the superbenzene and porphyrin moieties, but also behavior that differs distinctly from that of the individual buildung blocks. The molecule is characterized by standard spectroscopic methods and modern mass spectrometry, and the first X-ray structure of such a conjugate is presented.
Structurally characterized hetero-oligopolyphenylenes: Synthetic advances toward next-generation heterosuperbenzenes
Gregg, Daniel J.,Ollagnier, Cecile M. A.,Fitchett, Christopher M.,Draper, Sylvia M.
, p. 3043 - 3052 (2008/09/16)
The successful Diels-Alder [2+4] cycloaddition[1] of dipyrimidyl acetylene and suitably substituted 2,3,4,5-tetraarylcyclopenta-2,4-dien-lones (3-7) generates a series of selectively functionalized hexaarylbenzenes. Each has two pairs of peripheral functional groups (R' and R = tert-butyl 8 and R = methyl 9, methoxy 10, bromo 11, triisopropylsilylethynyl 12) and four ortho-imine nitrogen atoms. The dibromo derivative 11 is a useful precursor for the formation of a mono ethynyl 13 and diethynyl 14 substituted polyphen ylene. Changing the dienophile to di(2thienyl)acetylene gives an S-heteroatom polyphenylene 15. The compounds were fully characterized by using 1H, 13C and a range of 2D NMR spectroscopic techniques, elemental analysis, and mass spectrometry Oxidative cyclodehydrogenation of dimethoxy hexaphenylbenzene 10 by using iron(III) chloride results in the formation of a spirocyclic dienone 16, which in a separate reaction undergoes dienone/ phenol rearrangement to give the first 4-fused-ring, N-heterosuperbenzene (HSB) 17 Six single crystal molecular structures reveal the commonality of unidirectional twisting of the external aromatic rings in these heteroatom polyphenylenes. The twist angles and any H-bonding or interdigitation in these structures are discussed.
Syntheses of hexabenzocoronene derivatives
Sadhukhan, Subir K.,Viala, Christine,Gourdon, Andre
, p. 1521 - 1525 (2007/10/03)
The syntheses of four hexabenzo[bc,ef,hi,kl,no,qr]coronene (HBC) derivatives have been carried out. Double Knoevenagel condensation of the benzil 5 with the ketone 6 gave the 2,3,4,5-tetrakis(4-tert-butylphenyl)cyclopenta-2,4-dien-1-one (7). Diels-Alder a
