Intermolecular interaction energies (kcal mol⁻¹) of dimers in the packing structures of parent and β-MT-acenedithiophenes^a.

Compound		E es	E ex	E ind	E disp	E total
BDT	CH–π (edge-to-face)	−2.83	5.48	−0.83	−9.15	−7.33
β-MT-BDT	π-stacking	−7.05	14.59	−1.69	−21.31	−15.46
	π-stacking (w/o MT)b	−4.07	9.26	−0.87	−12.93	−8.60
	CH–π (end-to-face)	−2.48	5.76	−0.98	−7.35	−5.06
	S–H w/S–S contact (edge-to-edge)	−4.12	5.97	−0.71	−3.91	−2.77
	S–H w/o S–S contact (edge-to-edge)	−2.49	3.92	−0.60	−5.20	−4.36
NDT	CH–π (edge-to-face)	−4.06	7.99	−1.18	−13.67	−10.92
β-MT-NDT	π-stacking	−10.58	21.07	−2.28	−30.80	−22.59
	π-stacking (w/o MT)b	−6.23	15.66	−1.40	−21.93	−13.91
	CH–π (end-to-face)	−2.32	5.64	−0.95	−7.23	−4.88
	S–H w/S–S contact (edge-to-edge)	−5.36	8.84	−1.12	−8.03	−5.68
	S–H w/o S–S contact (edge-to-edge)	−1.03	3.49	−0.55	−5.66	−3.75
ADT	CH–π (edge-to-face)	−5.63	11.15	−1.66	−18.89	−15.03
β-MT-ADT	π-stacking	−10.47	22.30	−2.53	−32.16	−22.86
	π-stacking (w/o MT)b	−6.70	17.59	−1.75	−24.39	−15.26
	CH–π (end-to-face)	−2.94	6.62	−1.10	−9.63	−7.06
	S–H w/S–S contact (edge-to-edge)	−6.56	11.78	−1.45	−9.68	−5.91
	S–H w/o S–S contact (edge-to-edge)	−2.00	4.22	−0.65	−6.68	−5.11

^aObtained from zeroth-order symmetry-adapted perturbation theory (SAPT0) calculations with the jun-cc-pVDZ basis. E_es, E_ex, E_ind, E_disp, and E_total are electrostatic, exchange, induction, dispersion, and total intermolecular interaction energy, respectively. E_total = E_es + E_ex + E_ind + E_disp.

^bThe rows highlight the intermolecular interaction energies in the π-stacking dimers without (w/o) methylthio groups.