Synthetic Approach to and Characterization of a Fullerene–DTBT–Fullerene Triad

Maurizio D’Auria; Ambra Guarnaccio; Rocco Racioppi; Antonio Santagata; Roberto Teghil

doi:10.1055/s-0032-1316902

Synlett, Table of Contents

Synlett 2013; 24(8): 943-946
DOI: 10.1055/s-0032-1316902

letter

Synthetic Approach to and Characterization of a Fullerene–DTBT–Fullerene Triad

Maurizio D’Auria*

^aDipartimento di Scienze, Università della Basilicata, Viale dell’Ateneo Lucano 10, 85100 Potenza, Italy Fax: +39(0971)205678 Email: maurizio.dauria@unibas.it

,

Ambra Guarnaccio

^aDipartimento di Scienze, Università della Basilicata, Viale dell’Ateneo Lucano 10, 85100 Potenza, Italy Fax: +39(0971)205678 Email: maurizio.dauria@unibas.it

^bCNR-IMIP U.O.S. Potenza, Zona Industriale, 85100 Tito Scalo (PZ), Italy

,

Rocco Racioppi

^aDipartimento di Scienze, Università della Basilicata, Viale dell’Ateneo Lucano 10, 85100 Potenza, Italy Fax: +39(0971)205678 Email: maurizio.dauria@unibas.it

,

Antonio Santagata

^bCNR-IMIP U.O.S. Potenza, Zona Industriale, 85100 Tito Scalo (PZ), Italy

,

Roberto Teghil

^aDipartimento di Scienze, Università della Basilicata, Viale dell’Ateneo Lucano 10, 85100 Potenza, Italy Fax: +39(0971)205678 Email: maurizio.dauria@unibas.it

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Abstract

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Abstract

The synthesis of a new fullerene–dithienylbenzo[c]thiophene (DTBT)–fullerene triad is reported. The synthetic approach involves the synthesis of a DTBT unit, a Sonogashira reaction to introduce two acetylenic groups, and the coupling with fullerene. The product showed an absorption at λ = 485 nm and a fluorescence band at λ = 575 nm.

Key words

alkynes - arylation - fullerenes - heterocycles - palladium

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References

References and Notes
1 Katz HE, Bao Z, Gilat SL. Acc. Chem. Res. 2001; 34: 359

2a Waltman RJ, Bargon J. Can. J. Chem. 1986; 64: 76
2b Patil AO, Heeger AJ, Wudl F. Chem. Rev. 1988; 88: 183
2c Roncali J. Chem. Rev. 1997; 97: 173
2d Kraft A, Brimsdale AC, Holmes AB. Angew. Chem. Int. Ed. 1998; 37: 402
2e McCullough RD. Adv. Mater. 1998; 10: 93
2f Horowitz G. Adv. Mater. 1998; 10: 365
2g Garnier F. Acc. Chem. Res. 1999; 32: 209
2h Roncali J. J. Mat. Chem. 1999; 9: 1875
2i Bao Z. Adv. Mater. 2000; 12: 227
2j Groenendaal LB, Jonas F, Freitag D, Pielartzik H, Reynolds JR. Adv. Mater. 2000; 12: 481
2k Ma H, Jen AK.-Y. Adv. Mater. 2001; 13: 1201
2l Otsubo T, Aso Y, Takimiya K. Bull. Chem. Soc. Jpn. 2001; 74: 1789
2m van Mullekom HA. M, Vekemans JA. J. M, Havinga EE, Meijer EW. Mater. Sci. Eng. 2001; 32: 1
2n Otsubo T, Aso Y, Takimiya K. J. Mater. Chem. 2002; 12: 2565
2o Kelly TW, Baude PF, Gerlach C, Ender DE, Muyres D, Haase MA, Vogel DE, Theiss SD. Chem. Mater. 2004; 16: 4413
2p Newman CR, Frisbie CD, de Silva Filho DA, Brédas J.-L, Ewbank PC, Mann KR. Chem. Mater. 2004; 16: 4436
2q Ling MM, Bao Z. Chem. Mater. 2004; 16: 4824
2r Winder C, Sariciftci NS. J. Mater. Chem. 2004; 14: 1077
2s Barbarella G, Melucci M, Sotgiu G. Adv. Mater. 2005; 17: 1581
2t Facchetti A, Yoon M.-H, Marks TJ. Adv. Mater. 2005; 17: 1705
2u Perepichka IF, Perepichka DF, Meng H, Wudl F. Adv. Mater. 2005; 17: 2281
2v Sun Y, Liu Y, Zhu D. J. Mater. Chem. 2005; 15: 53
2w Anthony JE. Chem. Rev. 2006; 106: 5028
2x Roncali J, Leriche P, Cravino A. Adv. Mater. 2007; 19: 2045
2y Murphy AR, Fréchet JM. J. Chem. Rev. 2007; 107: 1066
2z Bundgaard W, Krebs FC. Sol. Energy Mater. Sol. Cells 2007; 91: 954

3a Ong BS, Wu Y, Li Y, Liu P, Pan H. Chem. Eur. J. 2008; 14: 4766
3b Arias AC, MacKenzie JD, McCulloch I, Rivnay J, Salleo A. Chem. Rev. 2010; 110: 3
3c D’Auria M. Adv. Heterocycl. Chem. 2011; 104: 127

4a Lorcy D, Cava MP. Adv. Mater. 1992; 4: 562
4b Bauerle P, Gotz G, Emerle P, Port H. Adv. Mater. 1992; 4: 564
4c Mohanakrishnan AK, Lakshmikantham MV, McDougal C, Cava MP, Baldwin JW, Metzger RM. J. Org. Chem. 1998; 63: 3105
4d Kiebooms R, Hoogmartens I, Adriaensens P, Vanderzande D, Gelan J. Macromolecules 1995; 28: 4961

5 Ertasa E, Ozturkb T. Tetrahedron Lett. 2004; 45: 3405
6 Musmanni S, Ferraris JP. J. Chem. Soc., Chem. Commun. 1993; 172
7 Piancatelli G, Scettri A, D’Auria M. Synthesis 1982; 245
8 1,2-Phenylenebis(2-thienylmethanol) (2) ¹H NMR (400 MHz, CDCl₃): δ = 7.44 (m, 2 H), 7.29 (m, 4 H), 7.17 (m, 2 H), 6.85 (m, 2 H), 6.695 (m, 2 H), 6.14 (s, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 147.27, 140.58, 128.78, 127.92, 127.07, 125.68, 125.31, 70.04. 1,2-Di-(2-thienoyl)benzene (3) ¹H NMR (400 MHz, CDCl₃): δ = 7.725 (m, 2 H), 7.635 (m, 4 H), 7.455 (m, 2 H), 7.055 (m, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 188.50, 144.28, 139.55, 135.36, 135.18, 130.83, 129.44, 128.23. GC–MS (EI): m/z = 298.0 [M⁺]. FT-IR (KBr pellet): ν_max = 1620, 1585, 1570, 1510, 1410 cm^–1. 1,3-Di-(2-thienyl)benzo[c]thiophene (4) ¹H NMR (400 MHz, CDCl₃): δ = 7.195 (m, 4 H), 7.195 (m, 3 H), 7.000 (m, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 135.57, 135.24, 127.86, 126.46, 125.57, 125.52, 124.76, 121.49. GC–MS (EI): m/z = 298.0 [M⁺]. UV-Vis (CHCl₃): λ_max = 435 nm. FT-IR (KBr pellet): ν_max = 1530, 1216, 1182, 841, 738 cm^–1.
9 Mitschke U, Bäuerle P. J. Chem. Soc., Perkin Trans. 1 2001; 740
10 Kisselev R, Thelakkat M. Chem. Commun. 2002; 1530
11 Jung YK, Kim H, Park J.-H, Lee J, Lee SK, Lee YS, Shim H.-K. J. Polym. Sci., Part A: Polym. Chem. 2008; 46: 3573
12 1,3-Bis(5-bromo-2-thienyl)benzo[c]thiophene (5) ¹H NMR (400 MHz, CDCl₃): δ = 7.87 (dd, J = 4 Hz, 2 H), 7.15 (d, J = 4 Hz, 2 H), 7.07 (m, 4 H). ¹³C NMR (100 MHz, CDCl₃): δ = 143.45, 136.99, 135.64, 130.95, 126.25, 125.50, 121.46, 112.59. GC–MS (EI): m/z = 455.8 [M⁺]. UV-Vis (CHCl₃): λ_max = 440 nm. FT-IR (KBr pellet): ν_max = 3062, 1529, 1489, 1433, 1190, 969, 788, 778, 734, 699, 582 cm^–1. 1,3-Bis[5-(2-trimethylsilylethynyl-2-thienyl)]benzo[c]-thiophene ¹H NMR (CDCl₃, 400 MHz): δ = 7.92 (dd, J = 4 Hz, 2 H), 7.22 (d, J = 4 Hz, 2 H), 7.15 (m, 4 H), 0.27 (s, 18 H). ¹³C NMR (100 MHz, CDCl₃): δ = 137.18, 135.71, 133.58, 126.70, 125.64, 125.24, 123.17, 121.78, 101.20, 97.50, 0.10. 1,3-Bis(5-ethynyl-2-thienyl)benzo[c]thiophene (6) ¹H NMR (500 MHz, CDCl₃): δ = 7.94 (dd, J = 5 Hz, 2 H), 7.35 (d, J = 5 Hz, 2 H), 7.25 (m, 4 H), 3.49 (s, 2 H). ¹³C NMR (125 MHz, CDCl₃): δ = 137.23, 135.67, 133.90, 126.44, 125.77, 125.02, 121.85, 121.47, 104.88, 82.94.
13 Benincori T, Brenna E, Sannicolò F, Trimarco L, Zotti G, Sozzani P. Angew. Chem., Int. Ed. Engl. 1996; 35: 648
14 Komatsu K, Murata Y, Takimoto N, Mori S, Sugita N, Wan TS. M. J. Org. Chem. 1994; 59: 6101
15 Lafleur-Lambert A, Rondeau-Gagné S, Soldera A, Morin JF. Tetrahedron Lett. 2011; 52: 5008
16 1,3-Bis(5-ethynyl-2-thienyl)benzo[c]thiophene–(C₆₀)₂ (7) ¹H NMR (400 MHz, CDCl₃): δ = 8.04 (m, 2 H), 7.93 (m, 2 H), 7.70, (m, 2 H), 7.38 (s, 2 H), 7.15 (m, 2 H), 6.98 (m, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 143.5, 142.3, 136.9, 134.8, 133.4, 130.4, 129.2, 129.1, 128.0, 128.8, 128.2, 128.1, 128.0, 127.9, 127.8, 127.6, 127.4, 127.3, 127.2, 127.1, 126.5, 126.3, 126.2, 126.27, 125.3, 125.31, 124.8, 124.6, 124.5, 125.5, 124.4, 124.1, 123.9, 123.7, 123.3, 123.2, 107.5, 79.5, 62.3, 54.9.
17 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision A.1 . Gaussian Inc; Wallingford (CT, USA): 2009

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