Synthesis, Inhaltsverzeichnis Synthesis 2012; 44(22): 3465-3476DOI: 10.1055/s-0032-1316785 paper © Georg Thieme Verlag Stuttgart · New YorkBenzothiadiazoloperylenes and Benzoxadiazoloperylenes: Amorphous Functional Materials Autoren Institutsangaben Heinz Langhals* Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 München, Germany Fax: +49(89)218077640 eMail: Langhals@lrz.uni-muenchen.de Fax: +49(89)218077680 eMail: Paul.Knochel@cup.uni-muenchen.de Paul Knochel Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 München, Germany Fax: +49(89)218077640 eMail: Langhals@lrz.uni-muenchen.de Fax: +49(89)218077680 eMail: Paul.Knochel@cup.uni-muenchen.de Andreas Walter Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 München, Germany Fax: +49(89)218077640 eMail: Langhals@lrz.uni-muenchen.de Fax: +49(89)218077680 eMail: Paul.Knochel@cup.uni-muenchen.de Silvia Zimdars Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 München, Germany Fax: +49(89)218077640 eMail: Langhals@lrz.uni-muenchen.de Fax: +49(89)218077680 eMail: Paul.Knochel@cup.uni-muenchen.de Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract 2,1,3-Benzothiadiazole or 2,1,3-benzoxadiazole were magnesiated (TMP2Mg·2LiCl) and efficiently attached to perylene and benzoperylene building blocks providing amorphous light-absorbing materials where FRET energy transfer proceeds between the 2,1,3-benzothiadiazole or 2,1,3-benzoxadiazole and the perylene units. Some of these new materials were obtained as amorphous solids of interest for material science. Key words Key wordsarenes - heterocycles - imides - cross-coupling fused-ring systems - zinc Volltext Referenzen References 1a Brabec CJ, Sariciftci NS, Hummelen JC. Adv. Funct. Mater. 2001; 11: 15 1b Günes S, Neugebauer H, Sariciftci NS. Chem. Rev. 2007; 107: 1324 1c Grätzel M. Nature (London) 2001; 414: 338 1d Choi H, Kim S, Kang SO, Ko J, Kang M.-S, Clifford JN, Forneli A, Palomares E, Nazeeruddin MK, Grätzel M. Angew. Chem. Int. Ed. 2008; 47: 8259 ; Angew. Chem. 2008, 120, 8283 1e Gao F, Wang Y, Shi D, Zhang J, Wang M, Jing X, Humphry-Baker R, Wang P, Zakeeruddin SM, Grätzel M. J. Am. Chem. Soc. 2008; 130: 10720 1f Gust D, Moore TA, Moore AL. Acc. Chem. Res. 2001; 34: 40 1g Wasielewski MR. J. Org. Chem. 2006; 71: 5051 Reviews: 2a Langhals H. Helv. Chim. Acta 2005; 88: 1309 2b Langhals H. Heterocycles 1995; 40: 477 2c Langhals H. Molecular Devices. Chiral, Bichromophoric Silicones: Ordering Principles in Complex Molecules. In Silicon Based Polymers. Ganachaud F, Boileau S, Boury B. Springer; Netherlands: 2008. Chap. 1, 51-63 For recent contributions, see: 3a Würthner F, Stolte M. Chem. Commun. 2011; 47: 5109 3b Osswald P, Reichert M, Bringmann G, Würthner F. J. Org. Chem. 2007; 72: 3403 3c You C.-C, Hippius C, Gruene M, Würthner F. Chem.–Eur. J. 2006; 12: 7510 3d Hiramoto M, Fukusumi H, Yokoyama M. Appl. Phys. Lett. 1992; 61: 2580 3e Zhan X, Facchetti A, Barlow S, Marks TJ, Ratner MA, Wasielewski MR, Marder SR. Adv. Mater. (Weinheim, Ger.) 2011; 23: 268 3f Zhao Y, Wasielewski MR. Tetrahedron Lett. 1999; 40: 7047 3g Oesterling I, Muellen K. J. Am. Chem. Soc. 2007; 129: 4595 3h Chen Z, Zheng Y, Yan H, Facchetti A. J. Am. Chem. Soc. 2009; 131: 8 4 Langhals H, Demmig S, Huber H. Spectrochim. Acta 1988; 44A: 1189 5a Langhals H, Kollefrath R, Lindner J. Macromol. Rep. 1995; A32: 415 5b Langhals H, Gold J. J. Prakt. Chem. 1996; 338: 654 5c Langhals H, Jona W. Angew. Chem. Int. Ed. 1998; 37: 952 ; Angew. Chem. 1998, 110, 998 6a Saragi TP. I, Spehr T, Siebert A, Fuhrmann-Lieker T, Salbeck J. Chem. Rev. 2007; 107: 1011 6b Silaghi SD, Spehr T, Cobet C, Saragi TP. I, Werner C, Salbeck J, Esser N. Appl. Phys. 2008; 103: 043503/1 7a Zimdars S, Langhals H, Knochel P. Synthesis 2011; 1302 7b Zimdars S PhD Dissertation; Universität München: Germany, 2011. 7c Zimdars S Diplomarbeit; Universität München: Germany, 2007. 8a Clososki GC, Rohbogner CJ, Knochel P. Angew. Chem. Int. Ed. 2007; 46: 7681 8b Rohbogner CJ, Clososki GC, Knochel P. Angew. Chem. Int. Ed. 2008; 47: 1503 9 Barder TE, Buchwald SL. Org. Lett. 2004; 6: 2649 10 Farina V, Krishnan B. J. Am. Chem. Soc. 1991; 113: 9585 11a Foerster T. Naturwissenschaften 1946; 33: 166 ; Chem. Abstr. 1947, 41, 36668 11b Foerster T. Ann. Phys. 1948; 2: 55 ; Chem. Abstr. 1949, 43, 31172 11c Foerster T. Z. Elektrochem. 1949; 53: 93 ; Chem. Abstr. 1949, 43, 33629 11d Foerster T. Z. Naturforsch. A 1949; 4: 321 ; Chem. Abstr. 1950, 44, 43074 12 Langhals H, Esterbauer AJ, Walter A, Riedle E, Pugliesi I. J. Am. Chem. Soc. 2010; 132: 16777 13 Langhals H, Karolin J, Johansson LB.-Å. J. Chem. Soc., Faraday Trans. 1998; 94: 2919 14 Kalinin S, Speckbacher M, Langhals H, Johansson LB.-Å. Phys. Chem. Chem. Phys. 2001; 3: 172
