Photophysical and theoretical investigations of the [8]cycloparaphenylene radical cation and its charge-resonance dimer

Golder, Matthew R.; Wong, Bryan M.; Jasti, Ramesh

doi:10.1039/c3sc51861b

Cited by 58 publications

(50 citation statements)

References 76 publications

(99 reference statements)

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“…5 Jasti et al observed the same spectra and attributed the broad absorption to the charge-resonance transition of a charge-resonance dimer (([8]CPP 2 ) •+ ). 6 Since the chargeresonance transition is expected to be nondegenerate and would not show the Faraday A term, their band assignment is inconsistent with the present results. In contrast to the intense MCD signals of the dication and radical cation, the MCD intensities of the neutral form were much weaker (Figure 1).…”

Section: Introductioncontrasting

confidence: 60%

“…Because of their unique topology, these macrocycles have attracted considerable attention, not only because of their theoretical interest, but also because of their possible applications in materials science. Since the first successful synthesis in 2008, 2 6 However, there is a significant discrepancy between the two reports regarding the band assignments of the oxidized species in the UV-VIS-NIR spectra; the dication and the radical cation in our study showed the same spectra as the radical cation and the dimer, respectively, reported by Justi. Herein, we report a definitive assignment of the absorption spectra of the dication and the radical cation by means of magnetic circular dichroism (MCD) spectroscopy, which can provide valuable information about the electronic structures of cyclic π-conjugated molecules.…”

Section: Introductioncontrasting

confidence: 58%

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In-Plane Aromaticity in Cycloparaphenylene Dications: A Magnetic Circular Dichroism and Theoretical Study

et al. 2014

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The electronic structures of [8]cycloparaphenylene dication ([8]CPP(2+)) and radical cation ([8]CPP(•+)) have been investigated by magnetic circular dichroism (MCD) spectroscopy, which enabled unambiguous discrimination between previously conflicting assignments of the UV-vis-NIR absorption spectral bands. Molecular orbital and nucleus-independent chemical shift (NICS) analysis revealed that [8]CPP(2+) shows in-plane aromaticity with a (4n + 2) π-electron system (n = 7). This aromaticity appears to be the origin of the unusual stability of the dication. Theoretical calculations further suggested that not only [8]CPP(2+) but also all [n]CPP (n = 5-10) dications and dianions exhibit in-plane aromaticity.

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Section: Introductioncontrasting

confidence: 60%

Section: Introductioncontrasting

confidence: 58%

In-Plane Aromaticity in Cycloparaphenylene Dications: A Magnetic Circular Dichroism and Theoretical Study

et al. 2014

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“…[58,59] Molar ratios of dipole (CF 3 ) to ion (imidazolium) of 1:1 and 2:1 were chosen for DFT calculations since these values bracket common experimental values. The ωB97X-D functional was specifically chosen due to its accurate description of both dispersion forces and thermochemistry for both neutral and ionic molecules.…”

Section: Doi: 101002/adma201605099mentioning

confidence: 99%

A Transparent, Self‐Healing, Highly Stretchable Ionic Conductor

et al. 2016

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Self-healing materials can repair damage caused by mechanical wear, thereby extending lifetime of devices. A transparent, self-healing, highly stretchable ionic conductor is presented that autonomously heals after experiencing severe mechanical damage. The design of this self-healing polymer uses ion-dipole interactions as the dynamic motif. The unique properties of this material when used to electrically activate transparent artificial muscles are demonstrated.

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“…Recently, Isobe reported tubular macrocycles, [4] Quite recently, the synthesis of CPPs was developed very rapidly and extensively by the groups of Itami, 12 Yamago, 13 Jasti, 14 and Müllen, 15 independently, and [5]- [16]CPPs and their derivatives were newly synthesized to explore characteristic properties. 16,17 Furthermore, the cavity of CPPs acts as a host for p-conjugated molecules, and C 60 was selectively encapsulated by [10]CPP, forming a 1 : 1 complex, [10]CPP*C 60 (Fig. Interestingly, [8]CPP 2+ showed in-plane aromaticity with 30p-electrons.…”

Section: Oligophenylene Macrocyclesmentioning

confidence: 99%

Multifunctional π-expanded oligothiophene macrocycles

2015

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This tutorial review summarizes recent progress in the design, synthesis, and multifunctional properties of fully conjugated macrocyclic π-systems. We focus on the π-expanded oligothiophene macrocycles after a short survey of macrocyclic conjugated loops and belts such as [n]cycloparaphenylenes, cyclic[n]para-phenylacetylenes, [4]cyclo-2,8-crysenylenes, and cyclo[n]thiophenes. Fully conjugated π-expanded oligothiophene macrocycles possess shape-persistent but sometimes pliable π-frames, and the electronic and optoelectronic properties of the macrocycles largely depend on the π-systems inserted into the oligothiophene macrocycles. Among them, the π-expanded oligothiophene macrocycle composed of 2,5-thienylenes, ethynylenes, and vinylenes is one of the most widely applicable macrocycles for constructing multifunctional π-systems. These π-expanded oligothiophene macrocycles from small to very large ring sizes can be prepared via a short step procedure, and their various solid state structures can be determined by X-ray analysis. Since these macrocycles have inner and outer domains, specific information concerning structural, electronic, and optical properties is expected. Furthermore, π-expanded oligothiophene macrocycles with alkyl substituents exhibit various morphologies depending on nanophase separation of molecules, and a morphological change is observed for the molecular switch.

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Photophysical and theoretical investigations of the [8]cycloparaphenylene radical cation and its charge-resonance dimer

Cited by 58 publications

References 76 publications

In-Plane Aromaticity in Cycloparaphenylene Dications: A Magnetic Circular Dichroism and Theoretical Study

In-Plane Aromaticity in Cycloparaphenylene Dications: A Magnetic Circular Dichroism and Theoretical Study

A Transparent, Self‐Healing, Highly Stretchable Ionic Conductor

Multifunctional π-expanded oligothiophene macrocycles

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