Spectroscopic studies and molecular orbital calculations on the charge transfer reaction between DDQ and 2-aminopyridine

Al-Ahmary, Khairia M.; Elkholy, Mohamed; Al-Solmy, Iman A.; Habeeb, Moustafa M.

doi:10.1016/j.saa.2013.03.055

Cited by 26 publications

(7 citation statements)

References 35 publications

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“…DDQ is one of a series of benzoquinones used as strong electron acceptors . Its EA is not as high as F4TCNQ, but it is highly soluble, more easily solution processable, and can be used as a p‐type dopant for trap filling or CTC formation . HATCN6 is a larger planar structure that is poorly solution processable and has been used to study the effect of electron acceptors on the work function of metal surfaces .…”

Section: Dopant Moleculesmentioning

confidence: 99%

Controlling Molecular Doping in Organic Semiconductors

2017

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The field of organic electronics thrives on the hope of enabling low-cost, solution-processed electronic devices with mechanical, optoelectronic, and chemical properties not available from inorganic semiconductors. A key to the success of these aspirations is the ability to controllably dope organic semiconductors with high spatial resolution. Here, recent progress in molecular doping of organic semiconductors is summarized, with an emphasis on solution-processed p-type doped polymeric semiconductors. Highlighted topics include how solution-processing techniques can control the distribution, diffusion, and density of dopants within the organic semiconductor, and, in turn, affect the electronic properties of the material. Research in these areas has recently intensified, thanks to advances in chemical synthesis, improved understanding of charged states in organic materials, and a focus on relating fabrication techniques to morphology. Significant disorder in these systems, along with complex interactions between doping and film morphology, is often responsible for charge trapping and low doping efficiency. However, the strong coupling between doping, solubility, and morphology can be harnessed to control crystallinity, create doping gradients, and pattern polymers. These breakthroughs suggest a role for molecular doping not only in device function but also in fabrication-applications beyond those directly analogous to inorganic doping.

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Section: Dopant Moleculesmentioning

confidence: 99%

Controlling Molecular Doping in Organic Semiconductors

2017

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“…The λ max of one of the CT bands, i.e., 584 nm for the complex in ANCHCl 3 and 587 nm in ANDCM, was chosen for quantitative measurements to provide the highest sensitivity. The radical anion of DDQ, which is intensely purple-colored, was produced in the studied solvents systems as a result of complete charge transfer from the donor (AMFP) to the acceptor (DDQ), as suggested in Scheme 1 [ 36 , 37 ]. This situation appears to be caused by the strong e-donating nature of AMFP, and the high electron affinity of DDQ (1.9 eV) [ 35 ].…”

Section: Resultsmentioning

confidence: 99%

New Charge Transfer Complexes of K+-Channel-Blocker Drug (Amifampridine; AMFP) for Sensitive Detection; Solution Investigations and DFT Studies

et al. 2021

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UV–Vis spectroscopy was used to investigate two new charge transfer (CT) complexes formed between the K+-channel-blocker amifampridine (AMFP) drug and the two π-acceptors 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) and tetracyanoethylene (TCNE) in different solvents. The molecular composition of the new CT complexes was estimated using the continuous variations method and found to be 1:1 for both complexes. The formed CT complexes’ electronic spectra data were further employed for calculating the formation constants (KCT), molar extinction coefficients (εCT), and physical parameters at various temperatures, and the results demonstrated the high stability of both complexes. In addition, sensitive spectrophotometric methods for quantifying AMFP in its pure form were proposed and statistically validated. Furthermore, DFT calculations were used to predict the molecular structures of AMFP–DDQ and AMFP–TCNE complexes in CHCl3. TD-DFT calculations were also used to predict the electronic spectra of both complexes. A CT-based transition band (exp. 399 and 417 nm) for the AMFP–TCNE complex was calculated at 411.5 nm (f = 0.105, HOMO-1 → LUMO). The two absorption bands at 459 nm (calc. 426.9 nm, f = 0.054) and 584 nm (calc. 628.1 nm, f = 0.111) of the AMFP–DDQ complex were theoretically assigned to HOMO-1 → LUMO and HOMO → LUMO excitations, respectively.

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“…Basic molecular modelling computations such as alignment, stochastic conformational sampling, dihedral driver and MM2 experiments can be effectively facilitated by using this software. Moreover, it can be used in prediction and visualization NMR, IR ,Raman and UV spectra [23][24][25][26][27][28].…”

Section: A N U S C R I P Tmentioning

confidence: 99%