A dual-mode photoswitching mechanism and charge transfer on chiroptical systems — theoretical study

Dantas, Socrates de Oliveira; Barone, P.M.V.B.; Braga, Scheila F.; Galvão, Douglas S.

doi:10.1016/s0379-6779(00)00466-5

Cited by 3 publications

(1 citation statement)

References 13 publications

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“…There is a great interest in molecular switching processes in part due to the possibility of optical information storage at the molecular level . The design of functional devices at the molecular level has been the object of intense theoretical and experimental research in the past years. − Among these systems, photochemically switchable bistable organic molecules have a special appeal due to their possible technological applications in reversible optical data storage and optical computing.…”

Section: Introductionmentioning

confidence: 99%

A Theoretical Investigation on the Dual-Mode Photoswitching Mechanism of Some Chiroptical Systems

Braga¹,

Galvão²,

Barone³

et al. 2001

J. Phys. Chem. B

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The synthesis of dual-mode optical molecular switching systems has been recently achieved. These systems were based on chiral helical-shaped alkenes in which the chirality can be reversibly modulated by light. In this work we report a theoretical study on the geometric and spectroscopic properties of these structures using the well-known semiempirical methods PM3 (parametric method 3) and ZINDO/S-CI (Zerner's intermediate neglect of differential overlap/spectroscopic-configuration interaction). Our results show that there are two stable conformers very close in energy for each possible molecular helicity presenting a barrier of ∼40 kcal/mol for bond rotation along the main molecular axis. Under protonation these barriers increase significantly and might explain why the protonation leads to the blocking of the switching process. We propose a scheme for the switching mechanism based on charge transfer and conformational changes during the isomer interconversion.

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Section: Introductionmentioning

confidence: 99%

A Theoretical Investigation on the Dual-Mode Photoswitching Mechanism of Some Chiroptical Systems

Braga¹,

Galvão²,

Barone³

et al. 2001

J. Phys. Chem. B

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Thiopyrans and their Benzo Derivatives

Hepworth

Heron

2008

Comprehensive Heterocyclic Chemistry III

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Dual-Mode Optical Molecular Switching Systems for Organic Memories

et al. 2001

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The synthesis of dual-mode optical molecular switching systems has been recently achieved. These systems were based on chiral helical-shaped alkenes in which the chirality can be reversibly modulated by light. In this work we report a theoretical study on the geometric and spectroscopic properties of these structures using the well-known semi-empirical methods PM3 (Parametric Method 3) and ZINDO/S-CI (Zerner's Intermediate Neglect of Differential Overlap -Spectroscopic - Configuration Interaction). Our results show that there are two stable conformers very close in energy for each possible molecular helicity presenting a barrier of ∼40 kcal/mol for bond rotation along the main molecular axis. Under protonation these barriers increase significantly and might explain why the protonation leads to the blocking of the switching process. We propose a scheme for the switching mechanism based on charge transfer and conformational changes during the isomer interconversion.

show abstract

A dual-mode photoswitching mechanism and charge transfer on chiroptical systems — theoretical study

Cited by 3 publications

References 13 publications

A Theoretical Investigation on the Dual-Mode Photoswitching Mechanism of Some Chiroptical Systems

A Theoretical Investigation on the Dual-Mode Photoswitching Mechanism of Some Chiroptical Systems

Thiopyrans and their Benzo Derivatives

Dual-Mode Optical Molecular Switching Systems for Organic Memories

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