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Synthesis, Structure, and Properties of ?-Vinyl Ketone/Ester Functionalized AzaBODIPYs from FormylazaBODIPYs.

ABSTRACT: Postfunctionalization of azaBODIPY (the BF₂ complex of azadipyrromethene) is highly desirable due to the strong tunable absorption bands at wavelengths above 650 nm and the wide-ranging applications of this class of dyes in biomedicine and materials science. Currently available postfunctionalization methods for this class of dyes have been limited to the Pd-catalyzed coupling reactions on ?-halogenated (brominated or iodinated) azaBODIPY platforms. In this work, we report a new strategy for the facile postfunctionalization of the azaBODIPY chromophore with various vinyl ketone and vinyl esters based on a Wittig reaction on our previously developed ?-formylazaBODIPYs and our recently developed ?-bromo-?'-formylazaBODIPYs. Our strategy uses easily accessible starting materials and mild reaction conditions. It is highly compatible with various common phosphonium ylides (aliphatic, aromatic, and ester substituted ones). These resultant bromo-containing ?-vinyl ketone/ester functionalized azaBODIPYs are potential photosensitizers and can be further functionalized via coupling reactions. The ester groups on some of these resultant azaBODIPYs can be further hydrolyzed to achieve the desired water solubility and conjugate with the biomolecule and solid surface.

SUBMITTER: Wang J

PROVIDER: S-EPMC6641003 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Synthesis, Structure, and Properties of β-Vinyl Ketone/Ester Functionalized AzaBODIPYs from FormylazaBODIPYs.

Wang Jun J Wu Yayang Y Sheng Wanle W Yu Changjiang C Wei Yun Y Hao Erhong E Jiao Lijuan L

ACS omega 20170608 6

Postfunctionalization of azaBODIPY (the BF<sub>2</sub> complex of azadipyrromethene) is highly desirable due to the strong tunable absorption bands at wavelengths above 650 nm and the wide-ranging applications of this class of dyes in biomedicine and materials science. Currently available postfunctionalization methods for this class of dyes have been limited to the Pd-catalyzed coupling reactions on β-halogenated (brominated or iodinated) azaBODIPY platforms. In this work, we report a new strate ...[more]

PMID: 31457601

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Project description:Three symmetrical bis-aryl-α,β-unsaturated ketone derivatives, 2,6-di((E)-benzylidene)-cyclohexan-1-one (DBC), 2,6-bis((E)-4-chlorobenzylidene)cyclohexan-1-one (BCC), and (1E,1'E,4E,4'E)-5,5'-(1,4-phenylene)bis(2-methyl-1-phenylpenta-1,4-dien-3-one) (PBMP), have been prepared using the aldol condensation approach toward ketones having two enolizable sites. The structures of DBC, BCC, and PBMP have been resolved via spectrometric methods. Moreover, the crystal structure of PBMP is determined by the single-crystal X-ray diffraction (SC-XRD) technique, which revealed that the PBMP molecular assembly is stabilized by the intermolecular C-H···O bonding and C-O···π and weak T-shaped offset π···π stacking interactions. The Hirshfeld surface analysis (HSA) of the PBMP crystal structure was performed as well, and the results were compared with the results of DBC and BCC. The density functional theory (DFT) study results revealed that the longer conjugated molecule of PBMP has smaller but still quite significant HOMO-LUMO gaps compared to the smaller molecules of BCC and DBC. The natural population analysis (NPA) and natural bonding orbital (NBO) analysis were performed. Accordingly, the hydrogen bonding and dipole-dipole interactions stabilize the crystal structures of these compounds. Additionally, the NBO analysis showed numerous high-energy stabilizing interactions for the PBMP compound due to the presence of numerous delocalized and relatively easily polarizable π-electrons, thus implying its significant thermodynamic stability. According to the global reactivity parameter (GRP) analysis, the compounds BCC and DBC are relatively stable in redox processes and have high thermodynamic stability and relatively lower reactivity in general. The molecular electrostatic potential (MEP) analysis results imply potential formation of the intermolecular hydrogen bonding and dispersion interactions, which stabilizes the crystal structures of these compounds.

Dataset Information

Synthesis, Structure, and Properties of ?-Vinyl Ketone/Ester Functionalized AzaBODIPYs from FormylazaBODIPYs.

Publications

Synthesis, Structure, and Properties of β-Vinyl Ketone/Ester Functionalized AzaBODIPYs from FormylazaBODIPYs.

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