Molecular structures and electronic properties of helical thiophene carbon-sulfur oligomers, H2(C2S)nC2H2 (n = 1-20)

Structural Chemistry

Volumn 21, Issue 4, 2010, Pages 715-725

  Wanno, Banchob ^a   Ruangpornvisuti, Vithaya ^b  

^a MAHASARAKHAM UNIVERSITY   (Thailand)

^b CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Chiral oligomer; Density functional theory; Electronic properties; Helical structure; Thiophene carbon sulfur

Indexed keywords

EID: 77954426031     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11224-010-9601-2     Document Type: Article

References (44)

1. Hartough HD, Meisel SL (1954) Compounds with condensed thiophene rings. Interscience Publishers, New York.
2. Kabir SMH, Miura M, Sasaki S, Harada G, Kuwatani Y, Yoshida M, Iyoda M (2000) Heterocycles 52: 761-774.
3. Allared F, Hellberg J, Remonen T (2002) Tetrahedron Lett 43: 1553-1554.
4. Nenajdenko VG, Gribkov DV, Sumerin VV, Balenkova ES (2003) Synthesis 1: 124-128.
5. Genin H, Hoffmann R (1995) J Am Chem Soc 117: 12328-12335.
6. Frapper G, Saillard J-Y (2000) J Am Chem Soc 122: 5367-5370.
7. Lee AWM, Yeung ABW, Yuen MSM, Zhang H, Zhao X, Wong WY (2000) Chem Commun 75-76.
8. Zmolek PB, Sohn H, Gantzel PK, Trogler WC (2001) J Am Chem Soc 123: 1199-1207.
9. Miyasaka M, Rajca A (2006) J Org Chem 71: 3264-3266.
10. Nenajdenko VG, Sumerin VV, Chernichenko KY, Balenkova ES (2004) Org Lett 6: 3437-3439.
11. Miyasaka M, Rajca A, Pink M, Rajca S (2005) J Am Chem Soc 127: 13806-13807.
12. Friedman TB, Cao X, Wang H, Rajca A, Nafie LA (2003) J Phys Chem A 107: 7692-7796.
13. Rajca A, Miyasaka M, Pink M, Wang H, Rajca S (2004) J Am Chem Soc 126: 15211-15222.
14. Miyasaka M, Rajca A, Pink M, Rajca S (2004) Chem Eur J 10: 6531-6539.
15. Rajca A, Rajca S, Pink M, Miyasaka M (2007) Synlett 1799-1822.
16. Collins SK, Vachon MP (2006) Org Biomol Chem 4: 2518-2524.
17. Torroba T, García-Valverde M (2006) Angew Chem Int Ed 45: 8092-8096.
18. Urbano A (2003) Angew Chem Int Ed 42: 3986-3989.
19. Collins SK, Grandbois A, Vachon MP, Côté J (2006) Angew Chem Int Ed 45: 2923-2926.
20. Grandbois A, Collins SK (2008) Chem Eur J 14: 9323-9329.
21. Míšek J, Teplý F, Stará IG, Tichý M, Šaman D, Císarová I, Vojtíšek P, Starý I (2008) Angew Chem Int Ed 47: 3188-3191.
22. Meurer KP, Vögtle F (1985) Top Curr Chem 127: 1-76.
23. Rajca A, Pink M, Xiao S, Miyasaka M, Rajca S, Das K, Plessel K (2009) J Org Chem 74: 7504-7513.
24. Osuna RM, Ortiz RP, Hernández V, Navarrete JTL, Miyasaka M, Rajca S, Rajca A, Glaser R (2007) J Phys Chem C 111: 4854-4860.
25. Becke AD (1993) J Chem Phys 98: 5648-5652.
26. Becke AD (1988) Phys Rev A 38: 3098-3100.
27. Lee C, Yang W, Parr RG (1988) Phys Rev B 37: 785-789.
28. Ruangpornvisuti V (2009) Int J Quantum Chem 109: 275-284.
29. Suwattanamala A, Ruangpornvisuti V (2009) Struct Chem 20: 619-631.
30. Kaenkaew S, Sae-Khow O, Ruangpornvisuti V (2010) Mol Mod 16: 243-253.
31. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2006) Gaussian 03, revision D02. Gaussian Inc., Pittsburgh, PA.
32. Li ZH, Moran D, Fan KN, Schleyer PvR (2005) J Phys Chem A 109: 3711-3716.
33. Dudev T, Lim C (1998) J Am Chem Soc 120: 4450-4458.
34. Sabin JR, Trickey SB, Apell SP, Oddershede J (2000) Int J Quantum Chem 77: 358-366.
35. Koopmans T (1933) Physica 1: 104-113.
36. Parr RG, Szentpaly Lv, Liu S (1999) J Am Chem Soc 121: 1922-1924.
37. Chattaraj PK, Pérez P, Zevallos J, Toro-Labbé A (2001) J Phys Chem A 105: 4272-4283.
38. Pérez P, Toro-Labbé A, Contreras R (2001) J Am Chem Soc 123: 5527-5531.
39. Chattaraj PK, Pérez P, Zevallos J, Toro-Labbé A (2002) J Mol Struct (Theochem) 580: 171-182.
40. Pérez P, Toro-Labbé A, Aizman A, Contreras R (2002) J Org Chem 67: 4747-4752.
41. Jaque P, Toro-Labbé A (2002) J Chem Phys 117: 3208-3219.
42. Wanno B, Ruangpornvisuti V (2005) Chem Phys Lett 415: 176-182.
43. Wanno B, Ruangpornvisuti V (2006) J Mol Struct (Theochem) 766: 159-164.
44. Wanno B, Ruangpornvisuti V (2006) J Mol Struct (Theochem) 775: 113-120.