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Sarkar, Abhijit; Pak, Joshua J.; Rayfield, G. W.; Haley, Michael M.

doi:10.1039/b107182n

Cited by 71 publications

(62 citation statements)

References 24 publications

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“…[41] With these systems one is able to tune the physical properties of the material to enhance a specific NLO response by varying the position of substituents on the system. It has been suggested that chromophores with threefold symmetry could give a higher first hyperpolarizability (β) value than linear dipolar compounds, which is desirable for second-order NLO properties.…”

Section: Functionalized [18]dbasmentioning

confidence: 99%

Synthetic Strategies for Dehydrobenzo[n]annulenes

2003

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Dehydrobenzoannulenes have accrued great interest due to their potential uses such as hosts for binding guest molecules and precursors to fullerenes and other carbon‐rich materials, as well as their unique properties such as conductivity or superconductivity and nonlinear optical effects. These systems have seen numerous synthetic strategies employed in their construction over the past 50 years. As alkyne chemistry has developed more recently, annulene networks with greater complexity have been possible and the field has seen a vast resurgence. This article gives an account of synthetic methods developed for the preparation of annulenic systems and describes some of the interesting observed properties. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Functionalized [18]dbasmentioning

confidence: 99%

Synthetic Strategies for Dehydrobenzo[n]annulenes

2003

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“…Regarding their highly conjugated structure, these compounds have intensively been studied [8][9][10][11][12][13][14] as promising candidates for innovative electronic and photonic materials [15]. The donor/ acceptor dehydrobenzo [18]annulenes attracted special interest given that this kind of push-pull systems is good candidates for use in non-linear optics [16,17]. At the same time, related donor/acceptor dehydrobenzo [12]annulenes remained unexplored with respect to their ability of providing a communication through the conjugated bridge.…”

Section: Introductionmentioning

confidence: 99%

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

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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.

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“…Structures 239-248 illustrate some of the various symmetries prepared and substituents utilized to date [80][81][82]. A representative synthesis, that of the C s -symmetric PDM 248, is shown in Scheme 8.53.…”

Section: Scheme 852mentioning

confidence: 99%

“…Furthermore, since these systems are also locked into planarity, the NLO efficiency is increased further, due to enhancement of p-conjugation and communication between chromophores. The b values for PDMs 1, 239, 242, 243, 245, and 248 have been measured by the hyper Raleigh scattering technique and were found to be two to three times greater than that of the standard 4-dimethylamino-4l-nitrostilbene reference chromophore [81].…”

Section: Scheme 852mentioning

confidence: 99%