Excimer and intramolecular charge transfer chemiluminescence from electrogenerated ion radicals of donor-acceptor stilbenoids

Chen, Chih-Yuan; Ho, Jau Der; Wang, Shunli; Ho, Tong‐Ing

doi:10.1039/b307331a

Cited by 27 publications

(18 citation statements)

References 19 publications

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“…Vinyl bonded AÀCH¼CHÀD derivatives have been reported to exhibit ECL behavior similar to that found for AÀC À À À CÀD molecules. [145][146][147] It should be noted, however, that ECL emission efficiencies observed for the above-listed linked donor-acceptor systems were smaller than reported for directly bounded A-D molecules. On the other hand, the mentioned examples shown clearly that the intramolecular donor-acceptor luminophores offer large flexibility in designing of new ECL systems.…”

Section: Organic Ecl Systems Electrochemical Excitation In Organic Eclmentioning

confidence: 68%

Electrochemiluminescent Systems as Devices and Sensors

Kapturkiewicz¹

2009

Electrochemistry of Functional Supramolecular Systems

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Section: Organic Ecl Systems Electrochemical Excitation In Organic Eclmentioning

confidence: 68%

Electrochemiluminescent Systems as Devices and Sensors

Kapturkiewicz¹

2009

Electrochemistry of Functional Supramolecular Systems

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“…Some studies have already investigated the generation of ECL through the direct attachment of a donor to an acceptor and have considered the possibility of the formation of charge‐transfer states 7, 8. Furthermore, the introduction of various types of π‐conjugated bridges in donor–acceptor luminescent molecules affords opportunities for investigating variations and new phenomena alike 9.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and DFT studies of donor–acceptor molecules containing phenylquinoline and phenothiazine moieties in various redox states

Ortiz

Osuna

Delgado

et al. 2005

Int J of Quantum Chemistry

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ABSTRACT:We report the ultraviolet (UV)-Vis, Fourier transform-infrared (FT-IR), and FT-Raman spectroscopic study of an electrogenerated chemiluminescence (ECL) emitting compound containing two electron-accepting phenylquinoline end groups covalently attached to an electron-donating 10-methylphenothiazine central moiety. The optimized molecular geometry of the neutral compound as determined from quantum chemical density functional theory (DFT)//B3LYP/3-21G* calculations shows that the phenyl groups appended onto the quinolines are twisted by Ϸ62°from these moieties. The sulfur atom is also tilted with respect to the plane defined by the phenyl rings of the phenothiazine, in both the neutral and singly oxidized species. The highest occupied molecular orbitals (HOMO) and lowest unoccupied molecular orbitals (LUMO) of the neutral systems partially overlap, so that the lowest-energy visible absorption band implies a certain degree of charge transfer from the phenothiazine toward the phenylquinolines. In contrast, the removal of the first electron mainly affects the structure and equilibrium charge distribution of the phenothiazine, and much less in those of the quinolines. In addition, the DFT//UB3LYP/3-21G* topologies of the molecular orbitals around the bandgap region of the radical cation reveal no molecular orbital overlap between the two types of constituent building blocks, thus inhibiting the delocalization of the injected positive charge over the whole molecule. This feature could be in line with the ability of this system to generate localized radical ions capable of displaying chemiluminescence upon annihilation, as previously observed experimentally. The UV-Vis and FT-Raman spectra of the singly oxidized species generated upon treatment with FeCl 3 in CH 2 Cl 2 solution have also been recorded. The experimental data were interpreted with the help of DFT calculations.

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“…A quite systematic studies have been performed for a series of the donor‐acceptor stilbenoids consisting N,N‐dimethylaniline as the donor and variety of small aromatic molecules as acceptors (Figure ) . Electrochemical properties of these molecules have been investigated in acetonitrile solutions with finding chemical irreversibility of their reduction and oxidation processes.…”

Section: Donor‐acceptor Ecl Systemsmentioning

confidence: 90%

“…Contrary to that, their ECL properties are distinctly less elaborated. Only the limited number of the stilbenoid derivatives have been investigated …”

Section: Donor‐acceptor Ecl Systemsmentioning

confidence: 99%

“…Usually the ECL emission maxima were somewhat red‐shifted due to presence of an additional long wavelength emission band from the excimer species. Only excimer type ECL emission was observed for 2‐( p ‐N,N‐dimethylamino)styrylthiophene . The ECL behavior of the reviewed stilbenoids were investigated only in a qualitative way, no data concerning efficiencies of their electrochemical excitation were given.…”

Section: Donor‐acceptor Ecl Systemsmentioning

confidence: 99%

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Electrochemical Generation of Excited Intramolecular Charge‐Transfer States

Kapturkiewicz

2017

ChemElectroChem

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intramolecular charge-transfer states have been attracting significant attention in recent decades, as they are crucial for different optoelectronic applications including the construction of efficient organic light-emitting devices. This possibility arises from the unique combination of the electrochemical and photophysical properties characterizing organic AÀD molecules, which contain the linked electron-donating D and electronaccepting A subunits. For the same reasons, the AÀD molecules are excellent luminophores that can be effectively excited in electrochemically generated chemiluminescence processes. This Review provides an overview of the current achievements in this particularly exciting field.

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Excimer and intramolecular charge transfer chemiluminescence from electrogenerated ion radicals of donor-acceptor stilbenoids

Cited by 27 publications

References 19 publications

Electrochemiluminescent Systems as Devices and Sensors

Electrochemiluminescent Systems as Devices and Sensors

Spectroscopic and DFT studies of donor–acceptor molecules containing phenylquinoline and phenothiazine moieties in various redox states

Electrochemical Generation of Excited Intramolecular Charge‐Transfer States

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