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Theoretical investigation on the effect of protonation on the absorption and emission spectra of two amine-group-bearing, red push-pull emitters, 4-dimethylamino-4′-nitrostilbene and 4-(dicyanomethylene)-2-methyl-6- p -(dimethylamino) styryl-4H-pyran, by DFT and TDDFT calculations

Theoretical investigation on the effect of protonation on the absorption and emission spectra of two amine-group-bearing, red push-pull emitters, 4-dimethylamino-4′-nitrostilbene and 4-(dicyanomethylene)-2-methyl-6- p -(dimethylamino) styryl-4H-pyran, by DFT and TDDFT calculations
Theoretical investigation on the effect of protonation on the absorption and emission spectra of two amine-group-bearing, red push-pull emitters, 4-dimethylamino-4′-nitrostilbene and 4-(dicyanomethylene)-2-methyl-6- p -(dimethylamino) styryl-4H-pyran, by DFT and TDDFT calculations

A theoretical investigation on the electronic structure of 4-dimethylamino-4′-nitrostilbene (DANS), 4-(dicyanomethylene)-2-methyl-6- p-(dimethylamino) styryl-4H-pyran (DCM), and their protonated forms is presented in an effort to rationalize recent experimental results on the tuning of the emitted color of organic light-emitting diodes through photochemically induced protonation. Density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations have been carried out on the neutral and protonated forms of DANS and DCM, employing both the B3LYP and the CAM-B3LYP functionals. It was found that the CAM-B3LYP functional leads to better agreement than the B3LYP of the calculated with the experimental absorption λmax for DANS, whereas B3LYP is more appropriate than CAM-B3LYP for DCM. The results of the calculations aid in a rationalization of the observed differences of the spectra of DANS and DCM upon protonation, and in particular those differences that make DANS a more attractive system for absorbance and emission tuning.

1089-5639
5580-5587
Petsalakis, I. D.
fa1d2c2e-5c95-40dc-ad85-85f0374402d4
Georgiadou, D. G.
84977176-3678-4fb3-a3dd-2044a49c853b
Vasilopoulou, M.
aad1381e-d091-4090-8c7c-b74bed22393d
Pistolis, G.
2a710db0-c97d-44bb-8ffc-896a7cd2a087
Dimotikali, D.
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Argitis, P.
ab9c4ea6-3dd2-4e34-935d-81bfb360f358
Theodorakopoulos, G.
cd4de8da-b206-4b04-8a25-d35108628cba
Petsalakis, I. D.
fa1d2c2e-5c95-40dc-ad85-85f0374402d4
Georgiadou, D. G.
84977176-3678-4fb3-a3dd-2044a49c853b
Vasilopoulou, M.
aad1381e-d091-4090-8c7c-b74bed22393d
Pistolis, G.
2a710db0-c97d-44bb-8ffc-896a7cd2a087
Dimotikali, D.
9c6d5002-c742-4576-b6dc-048acb0f1420
Argitis, P.
ab9c4ea6-3dd2-4e34-935d-81bfb360f358
Theodorakopoulos, G.
cd4de8da-b206-4b04-8a25-d35108628cba

Petsalakis, I. D., Georgiadou, D. G., Vasilopoulou, M., Pistolis, G., Dimotikali, D., Argitis, P. and Theodorakopoulos, G. (2010) Theoretical investigation on the effect of protonation on the absorption and emission spectra of two amine-group-bearing, red push-pull emitters, 4-dimethylamino-4′-nitrostilbene and 4-(dicyanomethylene)-2-methyl-6- p -(dimethylamino) styryl-4H-pyran, by DFT and TDDFT calculations. Journal of Physical Chemistry A, 114 (17), 5580-5587. (doi:10.1021/jp100338d).

Record type: Article

Abstract

A theoretical investigation on the electronic structure of 4-dimethylamino-4′-nitrostilbene (DANS), 4-(dicyanomethylene)-2-methyl-6- p-(dimethylamino) styryl-4H-pyran (DCM), and their protonated forms is presented in an effort to rationalize recent experimental results on the tuning of the emitted color of organic light-emitting diodes through photochemically induced protonation. Density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations have been carried out on the neutral and protonated forms of DANS and DCM, employing both the B3LYP and the CAM-B3LYP functionals. It was found that the CAM-B3LYP functional leads to better agreement than the B3LYP of the calculated with the experimental absorption λmax for DANS, whereas B3LYP is more appropriate than CAM-B3LYP for DCM. The results of the calculations aid in a rationalization of the observed differences of the spectra of DANS and DCM upon protonation, and in particular those differences that make DANS a more attractive system for absorbance and emission tuning.

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e-pub ahead of print date: 12 April 2010
Published date: 6 May 2010

Identifiers

Local EPrints ID: 440508
URI: http://eprints.soton.ac.uk/id/eprint/440508
ISSN: 1089-5639
PURE UUID: d08176f3-2119-4075-81ab-b8f7d2f58451
ORCID for D. G. Georgiadou: ORCID iD orcid.org/0000-0002-2620-3346

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Date deposited: 06 May 2020 16:30
Last modified: 07 Oct 2020 02:27

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Contributors

Author: I. D. Petsalakis
Author: M. Vasilopoulou
Author: G. Pistolis
Author: D. Dimotikali
Author: P. Argitis
Author: G. Theodorakopoulos

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