. Author manuscript; available in PMC: 2012 Jul 1.

Published in final edited form as: J Org Chem. 2011 May 27;76(13):5219–5228. doi: 10.1021/jo2005654

Table 3.

Electrochemical data for reference compounds E, F, 13 – 14, and cassette 3.

cmpd	E_onset,ox (V)	HOMO (eV)	E_onset,red (V)	LUMO (eV)	E_g (eV)
E^a	+0.68	5.84	−1.32	3.84	2.00
F^b	+0.33	5.48	−1.03	4.12	1.36
F_Na^b, ^d	+0.04	5.19	−1.67	3.48	1.71
13^a	+0.99	6.15	−0.91	4.28	1.87
14^b	+0.49	5.64	−0.93	4.22	1.42
14^c	+0.49	5.64	−0.92	4.23	1.41
3^a	+0.99	6.15	−0.92	4.24	1.91
3^a	+0.99	6.15	−1.18	3.98	2.17

Cyclic voltammograms were recorded using a glassy carbon working electrode (A = 0.071 cm²) referenced to Fc/Fc⁺ and a Pt counter electrode at a scan rate of 200 mV/s. All potentials are reported vs. Fc/Fc+ and all HOMO and LUMO energies are derived from electrochemical results based on Fc/Fc⁺ = 5.15 eV (DMF) and 5.16 eV (CH₂Cl₂) vs vacuum. All solvents were flushed with Ar_(g) before use.

In CH₂Cl₂.

In DMF.

In DMF and 0.1 M pyridine.

Xanthene was first reacted with NaOH to obtain the sodium salt.