Quantitative evaluation of solvation and packing effects on the visible absorption of anthraquinone derivatives

Abstract The solvatochromism of five anthraquinone compounds was evaluated at the TD-B3LYP level using the 6-31G(d,p) basis set whilst packing effects were investigated via an approach that combined semi-empirical and ab initio methods, namely ZINDO/TD-B3LYP/6-31G(d,p). This enabled calculation of the colourant's λ max with an average accuracy of 0.14 eV. The packing effects induced large changes in the UV/VIS spectra of the anthraquinones; large bathochromic and hyperchromic displacements were observed.

[1]  Shinichiro Nakamura,et al.  Calculation of the absorption wavelength of dyes using time-dependent density-functional theory (TD-DFT) , 2000 .

[2]  J. Tomasi,et al.  Quantum mechanical continuum solvation models. , 2005, Chemical reviews.

[3]  G. Scuseria,et al.  Hybrid functionals based on a screened Coulomb potential , 2003 .

[4]  Denis Jacquemin,et al.  Substitution effects on the visible spectra of 1,4-diNHPh-9,10-anthraquinones , 2005 .

[5]  Vincenzo Barone,et al.  Time-dependent density functional theory for molecules in liquid solutions , 2001 .

[6]  H. Schenk,et al.  Visible spectra of crystalline anthraquinone colorants: the impact of crystal packing , 2000 .

[7]  Kenneth B. Wiberg,et al.  A Comparison of the Electronic Transition Energies for Ethene, Isobutene, Formaldehyde, and Acetone Calculated Using RPA, TDDFT, and EOM-CCSD. Effect of Basis Sets , 2002 .

[8]  Julien Preat,et al.  Thioindigo dyes: highly accurate visible spectra with TD-DFT. , 2006, Journal of the American Chemical Society.

[9]  Parr,et al.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. , 1988, Physical review. B, Condensed matter.

[10]  Julien Preat,et al.  Theoretical investigation of substituted anthraquinone dyes. , 2004, The Journal of chemical physics.

[11]  V. Barone,et al.  A TDDFT study of the electronic spectrum of s-tetrazine in the gas-phase and in aqueous solution , 2000 .

[12]  X. Assfeld,et al.  Comparison of theoretical approaches for predicting the UV/Vis spectra of anthraquinones , 2007 .

[13]  K. A. Paseshnichenko,et al.  Experimental and computational structural study of two hindered aminoanthraquinones in crystals and solutions , 2000 .

[14]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[15]  Michael C. Zerner,et al.  An intermediate neglect of differential overlap technique for spectroscopy of transition-metal complexes. Ferrocene , 1980 .

[16]  Christian Silvio Pomelli,et al.  Recent Advances in the Description of Solvent Effects with the Polarizable Continuum Model , 1998 .

[17]  G. D. Nigam,et al.  Redetermination of the structure of 1,4-dihydroxyanthraquinone (C14H8O4) , 1980 .