ORGN 41 |
| Cyanoethynylethenes (CEEs) and 1,1,4,4-tetracyanobutadienes (TCBDs) are introduced as new classes of powerful organic electron acceptors. Upon peripheral substitution with strong electron donors, such as N,N-dialkylanilino moieties, a variety of interesting advanced materials properties are generated. They include expectional electron uptake and storage capacity, electronic transitions extending into the near infrared, strong nonlinear optical properties, and efficient two-photon absorption cross-sections. The new chromophores are obtained by short, atom-economic synthesis and feature high thermal and environmental stabilities. Multiple 1,1,4,4-tetracyanobutadiene moieties are introduced into the branches of dendritic phenylacetylenes, resulting in chromophores that undergo up to twenty and more one-electron reductions in a narrow potential range between ca. –0.5 and –1.5 V versus ferrocene. Donor-acceptor molecules with a strong dipole moment show antiparallel stacking in the crystalline state, and this order is also maintained in thin films obtained by vapor phase deposition. First device applications are introduced. |
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ACS Award for Creative Research and Applications of Iodine Chemistry: Symposium in Honor of Peter J. Stang
1:25 PM-5:00 PM, Sunday, March 25, 2007 McCormick Place Lakeside -- Room E451A/B, Level 4, Oral
Division of Organic Chemistry |