Synthesis of linearly-fused benzodehydro[12]annulenes

Gallagher, Megan E.; Anthony, John E.

doi:10.1016/s0040-4039(01)01591-x

Cited by 23 publications

(22 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The electronic absorption spectra of 1 (Fig. 5, Tables 3 and 4) exhibit the characteristic pattern found for dehydrobenzoannulene cores (1a in [18], alkoxy derivatives of 1a in [34] and 2a in [5]). The spectra of 1 are dominated by the band at w310 nm which presents a shift of w40 nm in comparison with the average location of the most prominent doublet in the spectrum of, for example, 3f.…”

Section: Uv/vis Spectramentioning

confidence: 66%

Spectroscopic properties of macrocyclic oligo(phenyldiacetylenes)-II. Synthesis and theoretical study of diacetylenic dehydrobenzoannulene derivatives with weak electron-donor and -acceptor groups

Zimmermann

Baranović

Štefanić

et al. 2006

Journal of Molecular Structure

View full text Add to dashboard Cite

Diacetylenic dehydrobenzo [12]annulene and dehydrobenzo [18]annulene derivatives with electron-donor and -acceptor groups were synthesized (including push-pull Eglinton-Galbraith dimer derivative 1c) via an oxidative coupling reaction, and spectroscopically and structurally characterized. The solid-solid phase transition in 1b has been revealed at 45 8C by DSC measurements. Its room temperature crystal structure has been solved by X-ray diffraction measurements. The 1 H and 13 C NMR chemical shifts, UV/vis and infrared absorption spectra and Raman scattering spectra have been analyzed by using ground-state DFT calculations. The strongest absorptions in the UV/vis spectra of 1 and 2 most probably are not due to the HOMO/LUMO excitations but due to the (HOMO-1)/LUMO and HOMO/(LUMOC1) excitations. The substitution effects on the electronic charge distribution of the all-carbon annulenic cores can be particularly well observed in the distribution of IR intensities in the region of acetylenic stretching vibrations. IR intensities are thus useful in studying the extent of resonance interactions also in acetylenic macrocycles.

show abstract

Section: Uv/vis Spectramentioning

confidence: 66%

Spectroscopic properties of macrocyclic oligo(phenyldiacetylenes)-II. Synthesis and theoretical study of diacetylenic dehydrobenzoannulene derivatives with weak electron-donor and -acceptor groups

Zimmermann

Baranović

Štefanić

et al. 2006

Journal of Molecular Structure

View full text Add to dashboard Cite

show abstract

“…[81] Figure 13 shows the representative compound 19, which was obtained as a ligand in a cyclopentadienyl-cobalt fragment in a mixture of products. Together with the fused porphyrins prepared by Crossley and Burn (20), [82] the open buckybelt from Schlüter and co-workers (21), [83] and the fused benzodehydro [12]annulene by Gallagher and Anthony (22), [84] these provide an impression of the structural diversity accessible. Recent examples by Moore and co-workers (23), [85] and Anderson and co-workers (24), [86,87] are noteworthy as they use dynamic covalent chemistry and supramolecular self-assembly, respectively.…”

Section: Multistranded Compounds With Low and High Molecular Weightmentioning

confidence: 99%

Two‐Dimensional Polymers: Just a Dream of Synthetic Chemists?

et al. 2009

View full text Add to dashboard Cite

In light of the considerable impact synthetic 2D polymers are expected to have on many fundamental and applied aspects of the natural and engineering sciences, it is surprising that little research has been carried out on these intriguing macromolecules. Although numerous approaches have been reported over the last several decades, the synthesis of a one monomer unit thick, covalently bonded molecular sheet with a long-range ordered (periodic) internal structure has yet to be achieved. This Review provides an overview of these approaches and an analysis of how to synthesize 2D polymers. This analysis compares polymerizations in (initially) a homogeneous phase with those at interfaces and considers structural aspects of monomers as well as possibly preferred connection modes. It also addresses issues such as shrinkage as well as domain and crack formation, and briefly touches upon how the chances for a successful structural analysis of the final product can possibly be increased.

show abstract

“…[63] Moreover, linearly fused [12]DBA systems, [n]acediynes 56 (n = 2) and 57 (n = 3), as well as the parent [12]DBA 45f were prepared by Anthony by intramolecular oxidative coupling of the corresponding precursors 58a-c, as shown in Scheme 6. [64] In contrast to 45f and 56, which are stable in both solution and the solid state, [3]acediyne 57 decomposes slowly in solution under aerobic conditions, while it is stable in the solid state. The absorptions of the acediynes extend to longer wavelengths with increasing numbers of [12]DBA units, like those of acenes.…”

Section: Strained Dehydrobenzo[12]annulenes ([12]dbas)mentioning

confidence: 99%

Strained Dehydrobenzoannulenes

2006

View full text Add to dashboard Cite

Dehydrobenzoannulenes (DBAs) have been attracting a great deal of interest as a result of their potential applications as optoelectronic materials, precursors of new forms of carbon materials, and as building blocks for hitherto‐unknown 2D carbon networks consisting of sp and sp2 carbon atoms. Among the DBAs, those with substantial strain due to bond‐angle deformation at the triple bonds exhibit greater potential as electronic communication units and precursors of new polycyclic, conjugated ring systems owing to their high reactivity towards carbon–carbon bond‐forming reactions. It is also of interest to see how the deformation of triple bonds affects the cyclic conjugation of π systems, that is, the aromaticity/antiaromaticity of DBAs. This article reviews these characteristic aspects of strained DBAs. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

show abstract

Synthesis of linearly-fused benzodehydro[12]annulenes

Cited by 23 publications

References 22 publications

Spectroscopic properties of macrocyclic oligo(phenyldiacetylenes)-II. Synthesis and theoretical study of diacetylenic dehydrobenzoannulene derivatives with weak electron-donor and -acceptor groups

Spectroscopic properties of macrocyclic oligo(phenyldiacetylenes)-II. Synthesis and theoretical study of diacetylenic dehydrobenzoannulene derivatives with weak electron-donor and -acceptor groups

Two‐Dimensional Polymers: Just a Dream of Synthetic Chemists?

Strained Dehydrobenzoannulenes

Contact Info

Product

Resources

About