Tetrathiafulvalene-thioindigo annelated donor–acceptor system with intramolecular charge transfer

Author:

Aqad Emad,Ellern Arkady,Shapiro Lev,Khodorkovsky Vladimir

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference8 articles.

1. Adam, M.; Müllen, K. Adv. Mater. 1994, 6, 439; Khodorkovsky, V.; Becker, J. Y. In Organic Conductors: Fundamentals and Applications; Farges, J. P., Ed.; Marcel Dekker: New York, 1994; Ch. 3, p. 75; Bryce, M. R. Adv. Mater. 1999, 11, 11.

2. Irie, M.; Kato, M. J. Am. Chem. Soc. 1985, 24, 1024; Fatah-ur Rahman, S. M. et al. Bull. Chem. Soc. Jpn. 1993, 66, 1461; Pawlik, A. et al. Angew. Chem., Int. Ed. Engl. 1994, 33, 1966; Schroth, W. et al. Chem. Ber. 1994, 127, 401; Gompper, R.; Hartmann, K.; Kellener, R.; Polborn, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 464.

3. Yeh, L.-S. R.; Brad, A. J. J. Electroanal. Chem. 1976, 70, 157; Memming, R.; Kobs, K. J. Phys. Chem. 1981, 85, 2771; Schanze, K. S.; Lee, L. Y. C.; Giannotti, C.; Whitten, D. G. J. Am. Chem. Soc. 1986, 108, 2646; Whitten, D. G. Photoinduced Electron Transfer; Elsevier, 1988; Part C, 53.

4. Aqad, E.; Ellern, A.; Khodorkovsky, V. Tetrahedron Lett. 1998, 39, 3311.

5. A shiny black plate (0.6×0.3×0.1 mm) of 3 is monoclinic: C18H10O2S8,, space group P21/n, Z=4, at 25°C, a=7.657(1), b=10.660(1), c=24.363(3) Å, β=90.54(1)°, V=1988.6(4) Å3, ρcalcd=1.719 Mg/m3, F(000)=1048. A total of 1080 frames were collected and integrated with a Bruker SAINT software package using a wide-frame integration algorithm. 20 315 reflections were collected (θ<21.98o), of which 2423 reflections were independent (Rint=20.44%) and 1578 with Fo>4σ(Fo). The structure was refined (255 parameters) to R1=4.61%, wR2=10.58%, GOF=0.939. A dark green plate (0.8×0.4×0.05 mm) of 6a is orthorhombic: C17H11NO3S7, space group P212121, Z=4, at 25°C, a=4.302(3), b=12.037(7), c=38.11(2) Å, V=1974(2) Å3, ρcalcd=1.688 Mg/m3, F(000)=1024. A total of 1080 frames were collected and integrated with Bruker SAINT software package using a wide-frame integration algorithm. 10151 reflections were collected (θ<24.93o), of which 3384 reflections were independent (Rint=11.11%) and 1985 with Fo>4σ(Fo). The structure was refined (255 parameters) to R1=5.43%, wR2=9.34%, GOF=0.881. Atomic coordinates, bond lengths and angles and thermal parameters have been deposited at the Cambridge Crystallographic Data Center.

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