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Electronic Supplementary Information (ESI)
for
Synthesis, Structure and Photophysical Properties of a
Supramolecular Complex with Gold Dicyanide Donors Coordinated
to Aza[5]helicene Viologen Acceptors
Ealin N. Patel,1 Robert B. Arthur,1 Aaron D. Nicholas,1 Eric W. Reinheimer,2 Mohammad A.
Omary,3 Matthew Brichacek,1* and Howard H. Patterson1*
1Department of Chemistry, University of Maine, Orono, ME 04469, 2Department of Chemistry and
Biochemistry and the W.M. Keck Foundation Center for Molecular Structure, California State
University, San Marcos, CA 92096 3Department of Chemistry, University of North Texas, Denton,
Synthesis details .........................................................................................................................1Figure S1. 1H NMR spectrum of 2 ...........................................................................................2Figure S2. 1H NMR spectrum of 4 ...........................................................................................3Figure S3. 13C NMR spectrum of 4 ..........................................................................................4Figure S4. 1H NMR spectrum of 5 ...........................................................................................5Figure S5. 13C NMR spectrum of 5 ..........................................................................................6Figure S6. 1H NMR spectrum of 6 ...........................................................................................7Figure S7. 1H NMR spectrum of 7a .........................................................................................8Figure S8. 13C NMR spectrum of 7a ........................................................................................9Figure S9. 1H NMR spectrum of 7b .........................................................................................10Figure S10. 13C NMR spectrum of 7b ........................................................................................11Figure S11. 1H NMR spectrum of 8 ...........................................................................................12Figure S12. 13C NMR spectrum of 8 ..........................................................................................13Figure S13. IR spectrum of microcrystalline Au heli-viologen at 298 K...................................14Table S1. Select bond lengths of Au heli-viologen.................................................................15Table S2. Select bond angles of Au heli-viologen. .................................................................16Table S3. DFT B3LYP/LANL2DZ select ground state parameters of Au heli-viologen.......17Figure S14. TD-DFT B3LYP/LANL2DZ calculated UV-vis of Au heli-viologen ...................18Table S3. TD-DFT calculated excited states of Au heli-viologen. .........................................19Table S4. Calculated MO transitions of Au heli-viologen for excited state at 399 nm ..........20Figure S15. MO transitions of excited state at 399 nm for Au heli-viologen. ...........................21
Synthesis details:
N
NN
N hv(350 nm)Photoreactor
EtOAcN
N+
5,10-diaza[5]helicene (5)
73% 19%
64
During the synthesis of 5,10-diaza[5]helicene (5), side-product- Benzo-[b]-1,8-diaza[4]-helicene
(6) was also recovered. Yield: 0.11 g (19%) 1H NMR (400 MHz, CDCl3) δ 11.37 (d, 1H,