. Author manuscript; available in PMC: 2015 Mar 1.

Published in final edited form as: Chem Sci. 2013 Dec 10;5(3):1008–1014. doi: 10.1039/C3SC53181C

Table 2.

Computational, electrochemical, and optical data for IDTs 7a–7d and diones 8a–8d

	Computational^a			Electrochemical^b					Optical^c
Compd	E_HOMO	E_LUMO	E_gap	E_red¹	E_red²	E_ox	E_HOMO	E_LUMO	E_gap	λ_max	E_Gap
7a	−5.35	−3.17	2.18	−0.92	−1.69^d	0.93	−5.57	−3.72	1.85	561	2.07
7b	−5.30	−3.34	1.96	−0.80	−1.62^d	0.92	−5.56	−3.84	1.72	624	1.88
7c	−5.41	−3.22	2.18	−0.94	−1.59^d	0.93^d	−5.57^d	−3.70	1.88	592	1.96
7d	−5.29	−3.46	1.84	−0.61	−1.24^d	0.98^d	−5.62^d	−4.03	1.59	632	1.83
8a^e	−6.12	−3.40	2.72	−0.91	−1.49	–	–	−3.73	–	566	1.75
8b^f	−5.99	−3.47	2.51	–	–	–	–	–	–	598	1.66
8c^e	−6.22	−3.41	2.81	−0.87	−1.27	–	–	−3.77	–	551	1.89
8d^f	−5.94	−3.51	2.43	–	–	–	–	–	–	609	1.56

Calculations were performed at the B3LYP/6-31G** level of theory; energies are in eV.

CVs were recorded using 1–5 mM of analyte in 0.1 M Bu₄NOTf/CH₂Cl₂ at a scan rate of 50 mV s⁻¹ with a glassy carbon working electrode, a Pt coil counter electrode, and a Ag wire pseudo-reference. Values reported as the half-wave potential (vs SCE) using the Fc/Fc⁺ couple (0.46 V) as an internal standard. HOMO and LUMO energy levels in eV were approximated using SCE = −4.68 eV vs vacuum (see ref 18) and E_1/2 values for reversible processes or E_p values for irreversible processes.

Spectra were obtained in DMSO; wavelengths are in nm. The optical HOMO/LUMO gap was determined as the intersection of the x-axis and a tangent line passing through the inflection point of the lowest-energy absorption; energies are in eV.

Reported as V at peak current, not half-wave potential.

Due to poor solubility in CH₂Cl₂, o-dichlorobenzene (ODCB) was used as solvent for electrochemical measurements.

Cyclic voltammetry measurements could not be obtained due to poor solubility of the compound.