A charge iteration-corrected extended-Hückel study of the electronic and spectroscopic properties of conjugatedheterocycles

Theoretical Chemistry Accounts

Volumn 121, Issue 1-2, 2008, Pages 43-52

  Castevens IV, Charles M ^a  

^a FPO AE 09532 2830 ^*  (United States)

Author keywords

CNDO S D; Extended H ckel; Indophenine; MCD; SEA STO 6G(d,p); UV visible

Indexed keywords

EID: 51749097765     PISSN: 1432881X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00214-008-0444-5     Document Type: Article

References (63)

1. Baeyer A (1879) Untersuchungen über die Gruppe des Indigblaus. Berl Dtsch Chem Ges 12: 1309-1319
2. Moore GE (1879) Report on the progress of analytical chemistry. J Am Chem Soc 1: 527-587
3. Meyer V (1882) Ueber Benzole verschiedenen Ursprungs. Berl Dtsch Chem Ges 15: 2893-2894
4. Meyer V (1883) Ueber den Begleiter des Benzols im Steinkohlentheer. Berl Dtsch Chem Ges 16: 1465-1478
5. Meyer V (1883) Untersuchungen über die Thiophengruppe. Berl Dtsch Chem Ges 16: 2172-2176
6. Meyer V (1888) Die thiophengruppe. Druck und Verlag Friedrich Vieweg und sohn, Braunschweig
7. Schlenk W, Blum O (1923) Über die konstitution des indophenins. Liebigs Ann Chem 433: 95-103
8. Heller GZ (1924) Zur konstitution des indophenins. Angew Chem 52: 1017-1018
9. Ray FE (1941) Organic chemistry. JP Lippincott, Chicago, p p 627
10. Ballantine JA, Fenwick RG (1970) A reinvestigation of the structure of indophenine. Some new evidence. J Chem Soc C 14: 2264-2266
11. Tormos GV, Belmore KA, Cava MP (1993) The indophenine reaction revisited. Properties of a soluble dialkyl derivative. J Am Chem Soc 115: 11512-11515
12. Glossman-Mitnik D (2007) CHIH-DFT determination of the molecular structure and infrared and ultraviolet spectra of azathiophenes. Theor Chem Acc 117: 57-68
13. Nåkansson R, Nordén B, Thulstrup EW (1977) Magnetic circular dichroism of heterocycles: thiophene. Chem Phys Lett 50: 306-308
14. Nordén B, Nåkansson R, Pedersen PB, Thulstrup EW (1978) The magnetic circular dichroism of five membered ring heterocycles. Chem Phys 33: 355-366
15. Kossmehl G, Manecke G (1968) Über die synthese polymerer indophenine und deren elektrische eigenschaften. Makromol Chem 113: 182-189
16. Martinez F, Naarmann H (1990) New oligomers with isatin. Condensation reactions of thiophene and 2,2'-bithiophene with isatin. Angew Makromol Chem 178: 1-16
17. Albinsson B, Kubista M, Nordén B, Thulstrup EW (1989) Near-ultraviolet electronic transitions of the tryptophan chromophore: linear dichroism, fluorescence anisotropy, and magnetic circular dichroism spectra of some indole derivatives. J Phys Chem 93: 6646-6654
18. 0 transitions. J Chem Phys 103: 9596-9606
19. Park H, Lee S, Hagberg DP, Marinado T, Karlsson KM, Nonomura K, Qin P, Bochloo P, Brinck T, Hagfeldt A, Sun L (2007) Tuning the HOMO and LUMO energy levels of organic chromophores for dye sensitized solar cells. J Org Chem 72: 9550-9556
20. Sobolewski AL, Domcke W (1999) Ab initio investigations on the photophysics of indole. Chem Phys Lett 315: 293-298
21. Wan J, Meller J, Hada M, Ehara M, Nakatsuji H (2000) Electronic excitation spectra of furan and pyrrole: Revisited by the symmetry adapted cluster-configuration interaction method. J Chem Phys 113: 7853-7866
22. Ramakrishna G, Bhaskar A, Bauerle P, Goodson III T (2008) Oligothiophene dendrimers as new building blocks for optical applications. J Phys Chem A 112: 2018-2026
23. da Silva JFM, Garden SJ, Pinto AC (2001) The chemistry of isatins: a review from 1975 to 1999. J Braz Chem Soc 12: 273-324
24. Tretiak S, Mukamel S (2002) Density matrix analysis and simulation of electronic excitations in conjugated and aggregated molecules. Chem Rev 102: 3171-3212
25. Casado J, Miller JJ, Mann KR, Pappenfus TM, Hernández V, López Navarrete JT (2002) Experimental and theoretical study of the infrared and Raman spectra of a substituted sexithiophene in five oxidation states. J Phys Chem B 106: 3597-3605
26. Can M, Özaslan H, Pekmez NÖ, Yildiz A (2003) Chemical synthesis of thiophene-pyrrole copolymer. Acta Chim Slov 50: 741-750
27. Stephens PJ (1970) Theory of magnetic circular dichroism. J Chem Phys 52: 3489-3516
28. Stephens PJ (1974) Magnetic circular dichroism. Ann Rev Phys Chem 25: 201-232
29. Wan J, Hada M, Ehara M, Nakatsuji H (2001) Electronic excitation spectrum of thiophene studied by symmetry-adapted cluster configuration interaction method. J Chem Phys 114: 842-850
30. Hariharan PC, Pople JA (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta 28: 213-222
31. Francl MM, Pietro WJ, Hehre WJ, Binkley JS, Gordon MS, DeFrees DJ, Pople JA (1982) Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements. J Chem Phys 77: 3654-3665
32. Shillady DD, Castevens CM, Trindle C, Sulik J, Klonowski P (2003) Conformational complexity of melatonin in water and methanol. Biophys Chem 105: 471-494
33. SYBYL 6.8, Tripos Inc., 1699 S Hanley RD, St. Louis
34. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA (1993) General atomic and molecular electronic structure system. J Comput Chem 14: 1347-1363
35. Gordon MS, Schmidt MW (2005) Advances in electronic structure theory: GAMESS a decade later. In: Dykstra CE, Frenking G, Kim KS, Scuseria GE (eds) Theory and applications of computational chemistry, the first forty years. Elsevier, Amsterdam
36. Shillady DD, Billingsley FP, Bloor JE (1971) Valence shell calculations on polyatomic molecules IV. The effect of deorthogonalization on CNDO/2 dipole moments and charge distributions. Theor Chim Acta 21: 1-8
37. Sprinkel FM, Shillady DD, Strickland RW (1975) MCD studies of indole, DL-tryptophan and serotonin. J Am Chem Soc 97: 6653-6657
38. Foresman JB, Head-Gordon M, Pople JA, Frisch MJ (1992) Toward a systematic molecular orbital theory for excited states. J Phys Chem 96: 135-149
39. Del Bene J, Jaffe HH (1968) Use of the CNDO method in spectroscopy. I. Benzene, pyridine, and the diazines. J Chem Phys 48: 1807-1813
40. Takata S, Ono Y, Ueda Y (1985) Extension of the CNDO/S method to the calculation of aromatic and heterocyclic compounds containing Si, P, S and Cl. Chem Pharm Bull 33: 3077-3091
41. Hug W, Wagnière G (1970) Molecular orbital calculations of rotational strengths: A study of skewed diketones. Theor Chim Acta 18: 57-66
42. ArgusLab 4.0.1, Mark A. Thompson, Planaria Software LLC, Seattle, http://www.arguslab.com
43. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery Jr., JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Rega N, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (2002) Gaussian 98, Revision A.11.3. Gaussian, Pittsburgh
44. Calzaferri G, Marcolli C (1995) Molecular geometries by the extended-Hückel molecular orbital method: A comment. J Phys Chem 99: 3895-3897
45. Calzaferri G, Rytz R (1995) Electronic transition oscillator strength by the extended Hückel molecular orbital method. J Phys Chem 99: 12141-12150
46. Rytz R, Glaus S, Brändle M, Brühwiler D, Calzaferri G (2000) ICON-EDiT 2000 manual, http://iacrs1.unibe.ch/program/iconedit.html
47. Calzaferri G, Fross L, Kamber I (1989) Molecular geometries by the extended Hückel molecular orbital method. J Phys Chem 93: 5366-5371
48. Bråndle M, Calzaferri G (1993) 166. Molecular geometries by the extended-Hückel molecular orbital method III: Band-structure calculations. Helv Chim Acta 76: 924-951
49. Seifert R, Kunzmann A, Calzaferri G (1998) Die gelbe farbe von silberhaltigem Zeolith A. Angew Chem 110: 1603-1606
50. Rytz R, Calzaferri G (1997) Electronic transition oscillator strengths in solids: an extended Hückel tight-binding approach. J Phys Chem B 101: 5664-5674
51. Palmer MH, Walker IC, Guest MF (1999) The electronic states of thiophene studied by optical (VUV) absorption, near-threshold electron energy-loss (EEL) spectroscopy and ab initio multi-reference configuration interaction calculations. Chem Phys 241: 275-296
52. Ohyama T, Mita H, Yamamoto Y (2005) Binding of 5,10,15,20-tetrakis (N-methylpyridinium-4-yl)-21H,23H-porphyrin to an AT-rich region of a duplex DNA. Biophys Chem 113: 53-59
53. Prieto I, Pedrosa JM, Martín-Romero MT, Möbius D, Camacho L (2000) Characterization and structure of molecular aggregates of a tetracationic porphyrin in LB films with a lipid anchor. J Phys Chem B 104: 9966-9972
54. Gouterman M (1961) Spectra of porphyrins. J Mol Spec 6: 138-163
55. Gouterman M, Wagnière GH, Snyder LC (1963) Spectra of porphyrins-part II. Four orbital model. J Mol Spec 11: 108-127
56. Susumu K, Maruyama H, Kobayashib H, Tanaka K (2001) Theoretical approach to the design of supramolecular conjugated porphyrin polymers. J Mater Chem 11: 2262-2270
57. Spitler EL, Shirtcliff LD, Haley MH (2006) Systematic structure-property investigations and ion-sensing studies of pyridine-derivatized donor/acceptor tetrakis(arylethynyl)benzenes. J Org Chem 72: 86-96
58. Zucchero AJ, Wilson JN, Bunz UHF (2006) Cruciforms as functional fluorophores: Response to protons and selected metal ions. J Am Chem Soc 128: 11872-11881
59. Sørensen JK, Vestergaard M, Kadziola A, Kilså K, Nielsen MB (2006) Synthesis of oligo (phenyleneethynylene)-tetrathiafulvalene cruciforms for molecular electronics. Org Lett 8: 1173-1176
60. Lopez X, Marques MAL, Castro A, Rubio A (2005) Optical absorption of the blue fluorescent protein: a first-principles study. J Am Chem Soc 127: 12329-12337
61. Holmquist B, Vallee BL (1973) Tryptophan quantitation by magnetic circular dichroism in native and modified proteins. Biochemistry 12: 4409-4417
62. McKee HC, Herndon K, Withrow JR (1948) Estimation of thiophene in gasoline. Anal Chem 20: 301-303
63. Thompson CJ, Coleman HJ, Mikkelsen L, Yee D, Ward CC, Hall HT (1956) Identification of thiophene and 2-methyl thiophene in virgin petroleum. Anal Chem 28: 1384-1387