Theoretical Study of Photochromic Compounds. 1. Bond Length Alternation and Absorption Spectra for the Open and Closed Forms of 29 Diarylethene Derivatives

Patel, Pansy D.; Masunov, Artëm E.

doi:10.1021/jp900485p

Cited by 62 publications

(50 citation statements)

References 56 publications

(76 reference statements)

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“…Patel and Masunov [114,115] employed TD-DFT with the linear response formalism to include continuum solvation to calculate absorption spectra of 29 diarylethene derivatives. They found that M05-2X gave the most accurate predictions of bond length alternation (see also [116]), and M05 at M05-2X geometries gave the best agreement with experiment for spectral data of both open and closed isomers.…”

Section: Excited Statesmentioning

confidence: 99%

Applications and validations of the Minnesota density functionals

Zhao

Truhlar

2011

Chemical Physics Letters

696

329

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Section: Excited Statesmentioning

confidence: 99%

Applications and validations of the Minnesota density functionals

Zhao

Truhlar

2011

Chemical Physics Letters

696

329

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“…6 Simple as it seems, accurately describing BLA is a challenge for many electronic structure methods. Trans-polyacetylene (referred to here as CC-II) is the most intensively studied system.…”

Section: Introductionmentioning

confidence: 99%

Double Hybrid Functionals and the Π-System Bond Length Alternation Challenge: Rivaling Accuracy of Post-HF Methods

Wykes

et al. 2015

J. Chem. Theory Comput.

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Predicting accurate bond-length alternations (BLAs) in long conjugated oligomers has been a significant challenge for electronic-structure methods for many decades, * To whom correspondence should be addressedThis is a previous version of the article published in Journal of Chemical Theory and Computation. 2015, 11(2): 832-838. doi:10.1021/ct500986b made particularly important by the close relationships between BLA and the rich optoelectronic properties of π-delocalized systems. Here we test the accuracy of recently developed, and increasingly popular, double-hybrid (DH) functionals, positioned at the top of Jacobs Ladder of DFT methods of increasing sophistication, computational cost and accuracy, due to incorporation of MP2 correlation energy. Our test systems comprise oligomeric series of polyacetylene, polymethineimine and polysilaacetylene up to six units long. MP2 calculations reveal a pronounced shift in BLAs between the 6-31g(d) basis set used in many studies of BLA to date, and the larger cc-pVTZ basis set, though only modest shifts between cc-pVTZ and aug-cc-pVQZ results. We hence perform new reference CCSD(T)/cc-pVTZ calculations for all three series of oligomers against which we assess the performance of several families of DH functionals based on BLYP, PBE and TPSS, along with lower-rung relatives including global-and rangeseparated hybrids. Our results show that DH functionals systematically improve the accuracy of BLAs relative to single-hybrid functionals. xDH-PBE0 (N 4 scaling using SOS-MP2) emerges as a DH functional rivalling the BLA-accuracy of SCS-MP2 (N 5 scaling), which was found to offer the best compromise between computational cost and accuracy last time the BLA accuracy of DFT-and wavefunction-based methods was systematically investigated. Interestingly, xDH-PBE0 (XYG3), which differs to other DHs in that its MP2 term uses PBE0 (B3LYP) orbitals which are not self-consistent with the DH functional, is an outlier of trends of decreasing average BLA errors with increasing fractions of MP2 correlation and HF exchange.

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“…Thus, the diarylethene derivatives have attracted much attention due to their potential applications in the future optoelectronic devices, such as highcapacity optical memories and ultrafast switches. [4][5][6] To realize such applications, many theoretical investigations have been carried out for revealing functionalities of the diarylethene derivatives, such as the reaction mechanism on excited states, [7][8][9][10][11][12] UV-vis spectra, [13][14][15][16][17][18][19][20][21] photoswitching of conductance, [22][23][24][25] and twophoton absorption. 26 We have also developed a parameter tuning scheme of density functional theory for reproducing the excitation energies of diarylethene derivatives well, 27,28 and have proposed a novel nonlinear optical property switching using open-shell singlet diarylethene derivatives.…”

Section: Introductionmentioning

confidence: 99%

Theoretical design of solvatochromism switching by photochromic reactions using donor–acceptor disubstituted diarylethene derivatives with oxidized thiophene rings

Okuno

Shigeta

Kishi

et al. 2015

Phys. Chem. Chem. Phys.

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We have designed several diarylethene derivatives with oxidized thiophene rings and donor-acceptor substituents, which show the solvatochromism switching by photochromic reactions, using a time-dependent density functional theory (TD-DFT) method using the polarizable continuum model (PCM). It is found that in the UV-vis spectral region examined only the open-ring isomers exhibit the solvatochromism, while the closed-ring isomers do not. The mechanism of the solvatochromism behavior and its switching process are clarified from the viewpoint of the charge-transfer (CT) excitation from the donor to the acceptor substituents. We demonstrate that this CT excitation can be controlled by choosing appropriate pairs of the donor and the acceptor substituents on the basis of the orbital correlation diagram between the diarylethene derivatives and the donor-acceptor substituents, which is constructed from the topologies and the orbital energies of the molecular orbitals primarily contributing to the excitations.

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Theoretical Study of Photochromic Compounds. 1. Bond Length Alternation and Absorption Spectra for the Open and Closed Forms of 29 Diarylethene Derivatives

Cited by 62 publications

References 56 publications

Applications and validations of the Minnesota density functionals

Applications and validations of the Minnesota density functionals

Double Hybrid Functionals and the Π-System Bond Length Alternation Challenge: Rivaling Accuracy of Post-HF Methods

Theoretical design of solvatochromism switching by photochromic reactions using donor–acceptor disubstituted diarylethene derivatives with oxidized thiophene rings

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