Electronic Structures and Theoretical Electronic Spcetra of Meso-Phenyl and 3,5-diaryl Substituted BODIPY Dyes

Abstract:

The electronic absorption spectra of four meso-phenyl and 3,5-diaryl substituted BODIPY dyes, A to D, were investigated theoretically using the time-dependent density functional theory (TD-DFT) B3LYP method. The dependence of spectra with the molecular and electronic structures was investigated on the basis 6-31+G*, 6-31G and 6-31G* in different solvents. The UV-Vis spectra were in good accordance with the experimental values. The maximum wavelengths of BODIPYs arose from S₀→S₁ transition which stemmed from HOMO to LUMO (π_{bodipy core}→π_{bodipy core}*).

• Periodical: Applied Mechanics and Materials (Volumes 716-717)
• Pages: 167-170
• DOI: https://doi.org/10.4028/www.scientific.net/AMM.716-717.167
• Online since: December 2014
• Authors: Gao Zhang Gou*, Ling Shi, Bo Zhou, Xian Lan Chen, Wei Liu, Chao Yong Mang
• Keywords: BODIPY Dyes, Density Functional Theory, Electronic Absorption Spectra

References

[1] Aurore Loudet, and Kevin Burgess. BODIPY dyes and their derivatives: syntheses and spectroscopic properties [J]. Chemical Reviews, 2007 107 (11) 4891-4932.

DOI: 10.1021/cr078381n

[2] Noël Boens, Volker Leen, and Wim Dehaen. Fluorescent indicators based on BODIPY [J]. Chemical Society Reviews, 2012 41 (3) 1130-1172.

DOI: 10.1039/c1cs15132k

[3] Lars H Thoresen, Heejin Kim, Mike B Welch, Armin Burghart, and Kevin Burgess. Synthesis of 3, 5-diaryl-4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY®) dyes [J]. Synlett, 1998 1998 (11) 1276-1278.

DOI: 10.1055/s-1998-1924

[4] Armin Burghart, Heejin Kim, Mike B Welch, Lars H Thoresen, Joe Reibenspies, Kevin Burgess, Fredrik Bergström, and Lennart B-Å Johansson. 3, 5-Diaryl-4, 4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) dyes: synthesis, spectroscopic, electrochemical, and structural properties [J]. The Journal of Organic Chemistry, 1999 64 (21) 7813-7819.

DOI: 10.1021/jo990796o

[5] Axel D Becke. Density-functional exchange-energy approximation with correct asymptotic behavior [J]. Physical Review A, 1988 38 (6) 3098.

DOI: 10.1103/physreva.38.3098

[6] Axel D Becke. Density‐functional thermochemistry. III. The role of exact exchange [J]. The Journal of Chemical Physics, 1993 98 5648.

DOI: 10.1063/1.464913

[7] Robert G Parr, and Weitao Yang, Density-functional theory of atoms and molecules [M]. Oxford university press, (1989).

[8] Frisch M J, Trucks G W and Schlegel H B, et al. Gaussian 09, Revision B. 01[CP], (Gaussian, Inc., Wallingford CT) (2010).

[9] S Miertuš, E Scrocco, and J Tomasi. Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects [J]. Chemical Physics, 1981 55 (1) 117-129.

DOI: 10.1016/0301-0104(81)85090-2

[10] B Mennucci, E Cances, and J Tomasi, Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: theoretical bases, computational implementation, and numerical applications [J]. The Journal of Physical Chemistry B, 1997 101 (49) 10506-10517.

DOI: 10.1021/jp971959k