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Resonant-convergent PCM response theory for the calculation of second harmonic generation in makaluvamines A-V: Pyrroloiminoquinone marine natural products from poriferans of genus Zyzzya
2015 (English)In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 119, no 21, 5368-5376 p.Article in journal (Refereed) Published
Abstract [en]

The first-order hyperpolarizability, β, has been calculated for a group of marine natural products, the makaluvamines. These compounds possess a common cationic pyrroloiminoquinone structure that is substituted to varying degrees. Calculations at the MP2 level indicate that makaluvamines possessing phenolic side chains conjugated with the pyrroloiminoquinone moiety display large β values, while breaking this conjugation leads to a dramatic decrease in the calculated hyperpolarizability. This is consistent with a charge-transfer donor-π-acceptor (D-π-A) structure type, characteristic of nonlinear optical chromophores. Dynamic hyperpolarizabilities calculated using resonance-convergent time-dependent density functional theory coupled to polarizable continuum model (PCM) solvation suggest that significant resonance enhancement effects can be expected for incident radiation with wavelengths around 800 nm. The results of the current work suggest that the pyrroloiminoquinone moiety represents a potentially useful new chromophore subunit, in particular for the development of molecular probes for biological imaging. The introduction of solvent-solute interactions in the theory is conventionally made in a density matrix formalism, and the present work will provide detailed account of the approximations that need to be introduced in wave function theory and our program implementation. The program implementation as such is achieved by a mere combination of existing modules from previous developments, and it is here only briefly reviewed. © 2015 American Chemical Society.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2015. Vol. 119, no 21, 5368-5376 p.
Keyword [en]
Charge transfer, Chromophores, Continuum mechanics, Harmonic generation, Nonlinear optics, Organic polymers, Radiation effects, Wave functions, Density matrix formalism, Dynamic hyperpolarizabilities, First-order hyperpolarizability, Marine natural products, Nonlinear optical chromophore, Polarizable continuum model, Solvent-solute interactions, Time dependent density functional theory, Density functional theory, biological product, pyrrole derivative, pyrroloiminoquinone derivative, solvent, animal, chemical model, chemical structure, chemistry, computer simulation, nonlinear system, photochemistry, sea, sponge (Porifera), Animals, Biological Products, Models, Chemical, Molecular Structure, Nonlinear Dynamics, Oceans and Seas, Photochemical Processes, Porifera, Pyrroles, Pyrroloiminoquinones, Solvents
National Category
Theoretical Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-198713DOI: 10.1021/jp5102362ISI: 000355495100033ScopusID: 2-s2.0-84930685607OAI: oai:DiVA.org:kth-198713DiVA: diva2:1059129
Note

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