Summary
A 1,1′-binaphthol based optically active oligomer 6 with 3,3′-acetylene spacer was prepared from 2,2′-dimethoxy-1,1′-binaphthalene 3 through the palladium-catalyzed Stille coupling reaction. The high optical rotation and CD spectrum varified the main chain chirality of the oligomer. The photophysical properties of 6, absorption, excitation and fluorescent spectra, demonstrated that the oligomer molecule had a conjugated structure, but twisting and rigid conformation would reduce the delocalization along the backbone.
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References
For the review on the optically active polymer from chiral monoer, see: Okamoto Y, Nakano T (1994) Chem Rev 94: 349 and Wulff G (1995) Angrew Chem Int Ed 34: 1812
For some recent example, see: Green M M, Peterson N C, Sato T, Teramoto A, Cook R, Lifson S (1995) Science 268: 1860; Puts R D, Sogah D Y (1995) Macromolecules 28: 390; Li L S, Strupp S I (1995) Macromolecules 28: 2618; Kakuchi T, Kamimura H., Matsunami S, Yokota K, Tsuda K (1995) Macromolecules 28: 658; Moore J S, Gorman C B, Grubbs R H (1991) J Am Chem Soc 113:1704; Coates G W, Waymouth R M (1991) J Am Chem Soc 113: 6270
Hu Q, Vitharana D, Liu G Y, Jain V, Wagaman M W, Zhang L, Lee T R, Pu L (1996) Macromolecules 29: 1082
Li C J, Wang D, Slaven IV W T (1996) Tetrahedron Letters 26: 4459
Bedworth P V, Tour J M (1994) Macromolecules 27: 622
Hu Q S, Vitharana D, Zheng X F, Wu C, Kwan C M S, Pu L (1996) J Org Chem 61: 8370;
Hu Q S, Zheng X F, Pu L (1996) J. Org. Chem. 61: 5200
For recent example, see: Sakamoto T,Yonehara H, Pac C (1994) J Org Chem 59: 6859; Niji M, Nakajima M, Koga K (1994) Tetrahedron Letters 35: 7983
Cox P J, Wang W, Snieckus V (1992) Tetrahedron Letters 17: 2253
For review, see: Stille J E (1986) Angew Chem Int Ed Engl 25: 508
Cummins C H (1994) Tetrahedron Letters 35: 857
Lingenfelter D S, Helgeson R C, Cram D J (1981) J Org Chem 46: 393
Langeveld-Voss B M W, Janssen R A J, Christiaans M P T, Meskers S C J, Dekkers H P J M, Meijier E W (1996) J Am Chem Soc 118: 4908
Moore J S, Gorman C B, Grubbs R H (1991) J Am Chem Soc 113: 1704
Hagler T W, Pakbaz K, Voss K F, Heeger A L (1991) Phys Rev B 8562
Mataga N, Yao H, Okada T, Rettig W (1989) J Phys Chem 93: 3383
Amotz D B, Harris C B (1987) J Chem Phys 86: 4856
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Wang, D., Liu, T.J., Li, C.J. et al. A chiral conjugated oligomer based on 1,1′-binaphthol with 3,3′-acetylene spacer. Polymer Bulletin 39, 265–270 (1997). https://doi.org/10.1007/s002890050147
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DOI: https://doi.org/10.1007/s002890050147