Conformational and electronic engineering of twisted diphenylacetylenes.

作者: Glen Brizius , Kelvin Billingsley , Mark D Smith , Uwe HF Bunz , None

DOI: 10.1021/OL035532+

关键词: ChemistryPhotochemistryQuantum yieldLinkerAlkyne metathesisDiphenylacetyleneSpectral lineFluorescenceCarbon-13 NMRAlkyne

摘要: Three tethered diphenylacetylene derivatives were prepared by alkyne metathesis. In these cycles, the twist angle between two benzene rings is variable and determined nature of linker. The engineering leads to a change UV−vis spectra cycles. larger in macrocycles, more blue shifted their λmax (UV−vis), lower fluorescence quantum yield, field 13C NMR signals carbons are.

参考文章(23)
Jonathan C. Collings, Karl P. Roscoe, Edward G. Robins, Andrei S. Batsanov, Lorna M. Stimson, Judith A. K. Howard, Stewart J. Clark, Todd B. Marder, Arene–perfluoroarene interactions in crystal engineering 8: structures of 1∶1 complexes of hexafluorobenzene with fused-ring polyaromatic hydrocarbons New Journal of Chemistry. ,vol. 26, pp. 1740- 1746 ,(2002) , 10.1039/B207102A
Geoffrey T. Crisp, Timothy P. Bubner, PREPARATION OF STERICALLY CONSTRAINED ARYLALKYNE OLIGOMERS Tetrahedron. ,vol. 53, pp. 11899- 11912 ,(1997) , 10.1016/S0040-4020(97)00762-X
Marcia Levitus, Kelli Schmieder, Holly Ricks, Ken D Shimizu, Uwe HF Bunz, Miguel A Garcia-Garibay, None, Steps To Demarcate the Effects of Chromophore Aggregation and Planarization in Poly(phenyleneethynylene)s. 1. Rotationally Interrupted Conjugation in the Excited States of 1,4-Bis(phenylethynyl)benzene Journal of the American Chemical Society. ,vol. 123, pp. 4259- 4265 ,(2001) , 10.1021/JA003959V
Sherri A. McFarland, Nathaniel S. Finney, Fluorescent signaling based on control of excited state dynamics. Biarylacetylene fluorescent chemosensors. Journal of the American Chemical Society. ,vol. 124, pp. 1178- 1179 ,(2002) , 10.1021/JA017309I
Uwe H. F. Bunz, Poly(p-phenyleneethynylene)s by alkyne metathesis. Accounts of Chemical Research. ,vol. 34, pp. 998- 1010 ,(2001) , 10.1021/AR010092C
J. Kim, T. M. Swager, Control of conformational and interpolymer effects in conjugated polymers. Nature. ,vol. 411, pp. 1030- 1034 ,(2001) , 10.1038/35082528
Uwe H. F. Bunz, Poly(aryleneethynylene)s: Syntheses, Properties, Structures, and Applications Chemical Reviews. ,vol. 100, pp. 1605- 1644 ,(2000) , 10.1021/CR990257J
Marcus Weck, Alex R. Dunn, Kozo Matsumoto, Geoffrey W. Coates, Emil B. Lobkovsky, Robert H. Grubbs, Influence of Perfluoroarene-Arene Interactions on the Phase Behavior of Liquid Crystalline and Polymeric Materials Angewandte Chemie International Edition. ,vol. 38, pp. 2741- 2745 ,(1999) , 10.1002/(SICI)1521-3773(19990917)38:18<2741::AID-ANIE2741>3.0.CO;2-1
Lioba Kloppenburg, Dschun Song, Uwe HF Bunz, None, Alkyne Metathesis with Simple Catalyst Systems: Poly(p-phenyleneethynylene)s Journal of the American Chemical Society. ,vol. 120, pp. 7973- 7974 ,(1998) , 10.1021/JA9813865
André Mortreux, Michel Blanchard, Metathesis of alkynes by a molybdenum hexacarbonyl–resorcinol catalyst Journal of The Chemical Society, Chemical Communications. pp. 786- 787 ,(1974) , 10.1039/C39740000786