Determination of the structure of 1,1′-diethyl-2,2′-carbocyanine iodide using NMR spectra and GIAO-HF/DFT calculations

Dyes and Pigments

Volumn 79, Issue 1, 2008, Pages 1-6

  Kim, Se Mi ^a   Kim, Dong Hee ^a  

^a Kunsan National University   (South Korea)

Author keywords

Carbocyanine; GIAO HF DFT; Molecular structure; NMR spectroscopy; PCYN; PES

Indexed keywords

CHEMICAL SHIFT; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE DIMENSIONAL; OPTIMIZATION; TWO DIMENSIONAL;

CARBOCYANINE IODIDE; PINACYANOL; QUINOLINE;

DYES;

INORGANIC COMPOUND; MAGNETIC RESONANCE IMAGING; MOLECULAR STRUCTURE; OPTIMIZATION;

EID: 41949104568     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2007.12.008     Document Type: Article

References (35)

1. Mishra A., Behera R.K., Behera P.K., Mishra B.K., and Behera G.B. Cyanines during the 1990s: a review. Chemical Reviews 100 6 (2000) 1973-2012
2. Adriaensen L., Vangaever F., and Gijbels R. A comparative study of carbocyanine dyes measured with TOF-SIMS and other mass spectrometric techniques. Applied Surface Science 231-232 (2004) 348-352
3. West W., Carroll B.H., and Whitcomb D.H. The adsorption of sensitizing dyes in photographic emulsions. Journal of Physical Chemistry 56 9 (1952) 1054-1067
4. Pugzlys A., Hania P.R., Augulis R., Duppen K., and van Loosdrecht P.H.M. Cylindrical aggregates of 5,5′,6,6′-tetrachlorobenzimidacarbocyanine amphiphilic derivatives: structure-related optical properties and exciton dynamics. International Journal of Photoenergy 2006 (2006) 1-9
5. Camposeo A., Persano L., Del Carro P., Virgili T., Cingolani R., and Pisignano D. Polarization splitting in organic-based microcavities working in the strong coupling regime. Organic Electronics 8 2-3 (2007) 114-119
6. Morishima S.-i., Warüshi K., Inagaki Y., Shibata M., Ishida T., and Kubo H. A new type of light stabilizer for dye layers of optical disks: tetracyanoquinodimethane derivatives. Japanese Journal of Applied Physics 38 3B (1999) 1634-1637
7. Ricceri R., Abbotto A., Facchetti A., Pagani G.A., and Gabrielli G. Langmuir-Blodgett films of a new pyridium-dicyanomethanide dye and their potential optical applications. Langmuir 13 13 (1997) 3434-3437
8. Kim B.G., Dai H.-N., McAtee M., Vicini S., and Bregman B.S. Labeling of dendritic spines with the carbocyanine dye Dil for confocal microscopic imaging in lightly fixed cortical slices. Journal of Neuroscience Methods 162 1-2 (2007) 237-243
9. Carreon J.R., Stewart K.M., Mahon Jr. K.P., Shin S., and Kelley S.O. Cyanine dye conjugates as probes for live cell imaging. Bioorganic and Medicinal Chemistry Letters 17 18 (2007) 5182-5185
10. Burke A., Schmidt-Mende L., Ito S., and Grätzel M. A novel blue dye for near-IR 'dye-sensitized' solar cell applications. Chemical Communications 3 (2007) 234-236
11. Zhan W.-H., Wu W.-J., Hua J.-L., Jing Y.H., Meng F.S., and Tian H. Photovoltaic properties of new cyanine-naphthalimide dyads synthesized by 'Click' chemistry. Tetrahedron Letters 48 14 (2007) 2461-2465
12. Makovitzky J., Bozsóky Jr. S., and László E. Topo-optical reactions of the human blood platelet membrane. Histochemistry and Cell Biology 79 2 (1983) 281-287
13. Sabate R., Gallardo M., de la Maza A., and Estelrich J. A spectroscopy study of the interaction of pinacyanol with n-dodecyltrimethylammonium bromide micelles. Langmuir 17 21 (2001) 6433-6437
14. Green M.D., Patonay G., Ndou T., and Warner I.M. Spectroscopic effects of organized media on a cyanine dye/pyrene derivative. Journal of Inclusion Phenomena and Macrocyclic Chemistry 13 2 (1992) 181-193
15. 2 nanocrystallites. Journal of Physical Chemistry B 104 15 (2000) 3616-3623
16. Yonezawa Y., and Ishizawa H. Luminescence properties of the mixed J-aggregate consisting of two kinds of thiacarbocyanine dyes or naphthothiacarbocyanine dyes having meso-substituent. Journal of Luminescence 69 3 (1996) 141-150
17. Du H., Fuh R.C.A., Li J.Z., Corkan L.A., and Lindsey J.S. PhotochemCAD: a computer-aided design and research tool in photochemistry. Photochemistry and Photobiology 68 2 (1998) 141-142
18. Werncke W., Tschol T.J., Weigmann H.J., Pfeiffer M., Lau A., Rentsch S., et al. Photoisomerization studies of pinacyanol using nanosecond time-resolved resonance cars. Journal of Raman Spectroscopy 18 5 (1987) 323-326
19. Kaupp M., Bühl M., and Malkin V.G. Calculation of NMR and EPR parameters: theory and applications (2004), Wiley-VCH, Weinheim
20. Bax A., and Freeman R. Investigation of complex networks of spin-spin coupling by two-dimensional NMR. Journal of Magnetic Resonance 44 (1981) 542-561
21. Bax A., and Summers M.F. Proton and carbon-13 assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. Journal of American Chemical Society 108 8 (1986) 2093-2094
22. Ditchfield R. Self-consistent perturbation theory of diamagnetism. Molecular Physics 27 4 (1974) 789-807
23. Cheeseman J.R., Trucks G.W., Keith T.A., and Frisch M.J. A comparison of models for calculating nuclear magnetic resonance shielding tensors. Journal of Chemical Physics 104 14 (1996) 5497-5509
24. Rablen P.R., Pearlman S.A., and Finkbiner J. A comparison of density functional methods for the estimation of proton chemical shifts with chemical accuracy. Journal of Physical Chemistry A 103 36 (1999) 7357-7363
25. Rauhut G., Puyear S., Wolinski K., and Pulay P. Comparison of NMR shieldings calculated from Hartree-Fock and density functional wave functions using gauge-including atomic orbitals. Journal of Physical Chemistry 100 15 (1996) 6310-6316
26. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., et al. Gaussian 98 Revision A.7 (1998), Gaussian, Inc., Pittsbugh, PA
27. Roothaan C.C.J. New developments in molecular orbital theory. Reviews of Modern Physics 23 2 (1951) 69-89
28. Pople J.A., and Nesbet R.K. Self-consistent orbitals for radicals. Journal of Chemical Physics 22 3 (1954) 571-572
29. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics 98 7 (1993) 5648-5652
30. Lee C., Yang W., and Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B 37 2 (1988) 785-789
31. * basis set for third-row atoms. Journal of Computational Chemistry 22 9 (2001) 976-984
32. Wolinski K., Hinton J.F., and Pulay P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of American Chemical Society 112 23 (1990) 8251-8260
33. Perdew J.P., Burke K., and Wang Y. Generalized gradient approximation for the exchange-correlation hole of a many-electron system. Physical Review B 54 23 (1996) 16533-16539
34. Lee M.J., and Kim D.H. Conformational study of liquid crystalline polymer: theoretical studies. Bulletin of the Korean Chemical Society 27 1 (2006) 39-43
35. Alkorta I., and Elguero J. Ab initio (GIAO) calculations of absolute nuclear shieldings for representative compounds containing 1(2)H, 6(7)Li, 11B, 13C, 14(15)N, 17O, 19F, 29Si, 31P, 33S, and 35Cl nuclei. Structural Chemistry 9 3 (1998) 187-202