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Organic & Biomolecular Chemistry Vol - 15 Issue - 3

Organic & Biomolecular Chemistry Vol - 15 Issue - 2

Organic & Biomolecular Chemistry Vol -9

Organic & Biomolecular Chemistry Vol -8

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Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

Push–pull pyropheophorbides for nonlinear optical imaging

Content Provider	Royal Society of Chemistry (RSC)
Author	Khadria, Anjul Gawel, Przemyslaw Anderson, Harry L. Clays, Koen Roche, Cécile Coene, Yovan de
Copyright Year	2017
Abstract	Pyropheophorbide-a methyl ester (PPa-OMe) has been modified by attaching electron-donor and -acceptor groups to alter its linear and nonlinear optical properties. Regioselective bromination of the terminal vinyl position and Suzuki coupling were used to attach a 4-(N,N-diethylaminophenyl) electron-donor group. The electron-acceptor dicyanomethylene was attached at the cyclic ketone position through a Knoevenagel condensation. Four different derivatives of PPa-OMe, containing either electron-donor or electron-acceptor groups, or both, were converted to hydrophilic bis-TEG amides to generate a series of amphiphilic dyes. The absorption and emission properties of all the dyes were compared to a previously reported push–pull type porphyrin-based dye and a commercial push–pull styryl dye, FM4-64. Electrochemical measurements reveal that the electron donor group causes a greater decrease in HOMO–LUMO gap than the electron-acceptor. TD-DFT calculations on optimized geometries (DFT) of all four dyes show that the HOMO is mostly localized on the donor, 4-(N,N-diethylaminophenyl), while the LUMO is distributed around the chlorin ring and the electron-acceptor. Hyper-Rayleigh scattering experiments show that the first-order hyperpolarizabilities of the dyes increase on attaching either electron-donor or -acceptor groups, having the highest value when both the donor and acceptor groups are attached. Two-photon excited fluorescence (TPEF) and second harmonic generation (SHG) images of the bis-TEG amide attached dyes in lipid monolayer-coated droplets of water-in-oil reveal that the TPEF and SHG involve transition dipole moments in different orientations.
Starting Page	947
Ending Page	956
Page Count	10
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	15
Issue Number	4
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c6ob02319c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Harmonic HOMO\/LUMO Regioselectivity Knoevenagel condensation HOMO Fluorescence FM4 Ketone Lipid Chlorin Ester Dye Suzuki Halogenation Dipole Amphiphile Amide Hydrophile Nonlinear optics Push\u2013pull train Suzuki reaction Nucleophile
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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