Evidence of Enhanced Conjugation in ortho-Arylene Ethynylenes with Transition Metal Coordination

The effective conjugation of ortho and ortho-alt-para-arylene ethynylenes, with appropriately positioned pyridine and pyrazine heterocycles, increases upon binding to Ag(I) and Pd(II) cations. Significant bathochromic shifts in the electronic spectra, witnessed upon introduction of these metal bridg...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 77; no. 5; pp. 2571 - 2577
Main Authors:	Ren, Qianwei, Reedy, Cole G, Terrell, Eric A, Wieting, Joshua M, Wagie, Robert W, Asplin, Jake P, Doyle, Leah M, Long, Steven J, Everard, Michael T, Sauer, Jon S, Baumgart, Cassandra E, D’Acchioli, Jason S, Bowling, Nathan P
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 02-03-2012
Subjects:	Alkynes - chemistry Chemistry Coordination compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Inorganic chemistry and origins of life Molecular Structure Organic chemistry Organometallic Compounds - chemical synthesis Organometallic Compounds - chemistry Palladium - chemistry Preparations and properties Pyrazines - chemistry Pyridines - chemistry Silver - chemistry Molecular rigidity Complexation Nitrogen heterocycle Palladium II Pyrazine derivatives Molecular interaction Electron delocalization Transition metal Pyridine derivatives Unsaturated compound Polyynic compound Acetylene derivative polymer Bathochromism Cations Aromatic compound Conjugated compound Spectrophotometry Silver I
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Summary:	The effective conjugation of ortho and ortho-alt-para-arylene ethynylenes, with appropriately positioned pyridine and pyrazine heterocycles, increases upon binding to Ag(I) and Pd(II) cations. Significant bathochromic shifts in the electronic spectra, witnessed upon introduction of these metal bridges, are consistent with enhanced electron delocalization in the unsaturated backbone. Control studies suggest that this electronic behavior is attributable exclusively (in the case of Ag(I)) or partially (in the case of Pd(II)) to conformational restrictions of the conjugated backbones.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo300034h