NDLI: Thiophene-Containing Pechmann Dyes and Related Compounds: Synthesis, and Experimental and DFT Characterisation

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Thiophene-Containing Pechmann Dyes and Related Compounds: Synthesis, and Experimental and DFT Characterisation

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Sullivan, Michael B. Ng, Joey J. Y. Kantchev, Eric Assen B. Norsten, Tyler B. Tan, Marilyn L. Y.
Description	Author Affiliation: Kantchev EA ( Institute of Materials Research and Engineering A*STAR, 3 Research Link, Singapore 117602, Singapore.)
Abstract	Attaching 2-thienyl residues to the Pechmann dye core chromophore (5,5-exo-dilactone situated around a CC double bond) results in a novel magenta-coloured compound (UV/Vis spectroscopy $λ_{max}=570 nm$ in $CHCl_{3}),$ which can be rearranged to a yellow 6,6-endo-dilactone $(λ_{max}=462 nm$ in $CHCl_{3}).$ Single and double amidation results in pronounced redshift in the 5,5-exo series (violet, $λ_{max}=570 nm$ and blue, $λ_{max}=606 nm$ in $CHCl_{3},$ respectively) but pronounced blueshift in the 6,6-endo series (yellow, $λ_{max}=424 nm$ and pale yellow bordering on colourless, $λ_{max}=395 nm$ in $CHCl_{3},$ respectively). Incorporation of a 3-alkyl substituent on the thiophene ring allows for sharp increase of solubility in organic solvents concomitant with fine-tuning of the colour: a redshift in 5,5-exo-dilactones but a blueshift in 5,5-exo-dilactams. DFT computations demonstrate that both lactone classes are planar regardless of the presence of a 3-alkyl group. The lactam derivatives are non-planar: the thiophene-core chromophore dihedral angles increase on going from 5,5-exo to 6,6-endo and from thiophene to 3-alkyl thiophene. Depending on the core heteroatom (O vs. N-alkyl), ring junction (5,5-exo vs. 6,6-endo) and 3-thiophene substituent (H vs. alkyl), two, three, four or six conformers are possible. All of these conformers were characterised by DFT and were found to be very close in energy at both IEFPCM/B3LYP/DGDZVP and SMD/M06/DGDZVP levels of theory. Within each conformer set, the HOMO and LUMO energies were within 0.05 eV and the predicted $λ_{max}$ values (TD-DFT) within 10 nm, and this implies low sensitivity of the optical and electronic properties to conformation. Cyclic voltammetry measurements of selected compounds demonstrated good matching to the HOMO and LUMO energies from IEFPCM/B3LYP/DGDZVP computations. M06-2X was the best DFT functional for TD-DFT, giving predicted $λ_{max}$ values within about 20 nm.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	2
Volume Number	18
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2012-01-09
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Coloring Agents Chemistry Thiophenes Chemical Synthesis Lactams Lactones Models, Molecular Quantum Theory Thermodynamics Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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