UV/Vis Spectra of Cyclophanes

Rademacher, Paul

doi:10.1002/3527603964.ch11

Cited by 13 publications

(2 citation statements)

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“…There is strong evidence that the two benzene rings in [2,2]paracyclophane are in conjugation. The small HOMO−LUMO gap (UV, λ max = 302 nm) and the photoelectron spectrum , indicate a strong through-bond or through-space interaction. Substituents at the benzene rings affect not only the 1 H NMR chemical shift of the ortho protons but also the chemical shifts of the opposing unsubstituted ring …”

Section: 3 Paracyclophanementioning

confidence: 99%

Anisotropy of the Induced Current Density (ACID), a General Method To Quantify and Visualize Electronic Delocalization

et al. 2005

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Section: 3 Paracyclophanementioning

confidence: 99%

Anisotropy of the Induced Current Density (ACID), a General Method To Quantify and Visualize Electronic Delocalization

et al. 2005

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“…Along with their planar chirality, [2.2]paracyclophanes possess interesting photophysical properties that arise from through‐space and through‐bond conjugation between their two aromatic rings. [ 50 ] Commercially available pCp indeed displays an unusual UV‐visible spectrum, with absorption maxima at 225, 244, 286, and 302 nm. [ 51 ] Its most redshifted absorption band, called “ cyclophane band ”, is displaced into a wavelength region rarely observed for more common benzene derivatives.…”

Section: Tuning the Photophysical Behaviors Of Pcpsmentioning

confidence: 99%

[2.2]Paracyclophanes: From Selective Functionalization to Optical Properties

Wu,

Felder,

Brom

et al. 2024

Advanced Optical Materials

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Since their discovery, [2.2]paracyclophane (pCp) and its derivatives have fascinated the scientific community due to their original molecular architecture and unusual electronic behavior. Over the years, significant efforts have been devoted to the development of substituted pCps for a variety of applications in different fields, ranging from organic synthesis and asymmetric catalysis to polymer chemistry and material science. This review describes a series of useful approaches that allow chemists to selectively decorate pCps, control the planar chirality that these molecules can display as soon as they are functionalized, and tune their photophysical behaviors. For each of these aspects of paracyclophane chemistry, selected examples of major advances are presented, and possible directions for future research are outlined. The application of pCp as central core for the development of uncommon 3D luminophores is finally highlighted. Emphasis is placed on the potential use of planar chiral luminescent paracyclophanes as antennas or ligands for the design of multifunctional lanthanide complexes, a quite underdeveloped but highly promising area for future research endeavors.

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