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1 Supporting Information for Definitive evidence for the contribution of biradical character in closed-shell molecule, derivative of 1,4-bis-(4,5-diphenylimidazol-2-ylidene)cyclohexa-2,5-diene Azusa Kikuchi, umiyasu Iwahori and Jiro Abe* Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University, and The 21st Century COE Program, uchinobe, Sagamihara, Kanagawa , Japan
2 1. Preparation of t-bdpi-2y and t-bdpi-2yd Materials: All reactions were monitored by thin-layer chromatography carried out on 0.2 mm E. Merck silica gel plates (60-254). Column chromatography was performed on silica gel (E. Merck, mesh). Materials were purchased from TCI and Wako Co. Ltd., and were used without further purification. Chloroform was dried and distilled from CaH 2 and benzene was dried and distilled from sodium / benzophenone. (i) To a stirring solution of 1,2,4,5-tetrafluorobenzene ((1) 13.5 g, mol) in dehydrated chloroform was added anhydrous aluminum (III) chloride (75.0 g, mol). The reaction mixture was refluxed for 12 h and then poured into cold water, extracted with chloroform. The chloroform extract was washed with water, dried over magnesium sulfate, and concentrated to give 1,4-bis(dichloromethyl)-2,3,5,6-tetrafluorobenzene(2) as a pale yellow powder. The obtained powder was purified on column chromatography, using hexane as eluent. Recrystallization from hexane gave 1 in 65 % yield (18.5 g) as colorless plate crystal: 1 H MR(CDCl 3, 500 MHz): δ 6.96 (s, 2H). (ii) A solution of 2 (5.00 g, 15.8 mmol) and iron(iii) sulfate heptahydrate(0.792 g, 2.85 mmol) in concentrated sulfuric acid was heated to 150 C for 6 h and then poured into cold water. The aquaous solution was extracted with chloroform. The chloroform extract was washed with water, dried over magnesium sulfate, and concentrated to give 2,3,5,6-tetrafluorotelephthalaldehyde(3) as a pale yellow powder. The obtained powder was purified on colunm chromatography, using chloroform as eluent. Recrystallization from chloroform gave 3 in 55 % yield (1.79 g) as colorless needle crystals: 1 H MR(CDCl 3, 500 MHz): δ (s, 2H). (iii) Under nitrogen, to a stirring solution of 3 (0.500 g, 2.45 mmol), benzil (1.07 g, 5.09 mmol) and ammonium acetate (3.74 g, 48.5 mmol) in acetic acid (55 ml) was heated to reflux, giving a light yellow clear solution. After 15 min the reaction mixture becomes a brown-orange solution and cloudy, and then a pale yellow precipitate forms. After 12 h the reaction was stopped, and the mixture was cooled. The solid was filtered, washed with hexane. Recrystallization from chloroform containing a little ethanol gave 1,4-bis(4,5-diphenylimidazolyl-2-yl)tetrafluorobenzene (t-bdpi-2y-lophine) in 20 % yield (0.285 g) as pale-yellow crystals. 1 H MR(CDCl 3, 500 MHz): δ (s, 2H), (m, 20H) ; Anal.Calcd for C 36 H : C, 73.71; H, 3.78;, 12.96;, ound: C, 73.43; H, 3.97;, (iv) To a solution of t-bdpi-2y-lophine (0.150 g, mmol) in benzene (500 ml) containing aqueous potassium hydroxide (2, 300 ml) was dropped aqueous potassium ferricyanide (5.25 g, 13.3 mmol, 200 ml) in a period of 0.5 h. After addition of aqueous potassium ferricyanide, the organic layer - 2 -
3 becomes purple solution. The reaction mixture was stirred for an additional 1 day at room temperature. The organic layer was separated, washed with water, dried over calcium chloride, and concentrated to give 3,6-bis(4,5-diphenyl-2H-imidazol-2-ylidene)-1,2,4,5-tetrafluorocyclohexa-1,4-diene (t-bdpi-2y) in 92 % yield (0.138 g) as blue-purple microcrystals. Recrystallization from hot benzene gave t-bdpi-2yd in 35 % yield (0.050 g) as colorless plate crystals. H H i Cl 2 HC CHCl 2 ii OHC CHO iii H H t-bdpi-2y-lophine iv hν t-bdpi-2y t-bdpi-2yd Scheme S1 i. AlCl 3, CHCl 3, 70 C, 1 day, yield (65 %); ii. eso 4 7H 2O, H 2SO 4, 150 C, 6 h, yield (55 %); iii. benzil, CH 3COO - H 4 + -CH 3COOH, 130 C, 1 day, (20 %); iv. K 3[e(C) 6], KOHaq-benzene, r.t., 1 day, (92 %)
4 2. DT calculations for t-bdpi-2y and t-bdpi-2yd The molecular structures were fully optimized at the Beck3LYP/6-31G(d) level of theory. The total SC energies and S 2 for the triplet state are summarized in Tables S1, S2. The optimized geometries are summarized in Tables S3-S6. Table S1. Becke3LYP/6-31G(d) SC energies and S 2 for the closed-shell singlet and open-shell triplet states for BDPI-2Y. State SC Energy [Hartree] S 2 Closed-shell singlet (RBLYP) 0.0 Open-shell triplet (UBLYP) Table S2. Becke3LYP/6-31G(d) SC energies and S 2 for the closed-shell singlet and open-shell triplet states for t-bdpi-2y. State SC Energy [Hartree] S 2 Closed-shell singlet (RBLYP) 0.0 Open-shell triplet (UBLYP)
5 Table S3. The optimized Cartesian coordinates for the closed-shell singlet state for BDPI-2Y. C C C C C C H C C H C H C H H H C C C C C C H C C C C H H H H H C H C H C H C H C C C C C H C H C H C H C H C H C H C H
6 Table S4. The optimized Cartesian coordinates for the open-shell triplet state for BDPI-2Y. C C C C C C H C C H C H C H H H C C C C C C H C C C C H H H H H C H C H C H C H C C C C C H C H C H C H C H C H C H C H
7 Table S5. The optimized Cartesian coordinates for the closed-shell singlet state for t-bdpi-2y. C C C C C C C C H C H C H H C C C C C C C C C C H H H H C H C H C H C H C C C C C H C H C H C H C H C H C H C H
8 Table S6. The optimized Cartesian coordinates for the open-shell triplet state for t-bdpi-2y. C C C C C H H C C C C C C C C C H H C C H C H C C C H H C C C C C H C H C H C H C C C H C H C C C H C H H H H H
9 igure S1. SOMOs for the open-shell triplet state of t-bdpi-2y calculated by the UB3LYP/6-31G(d) method. SOMO 1 SOMO 2 3. ESR measurements for the light-irradiated toluene solution of t-bdpi-2yd and the toluene solution of BDPI-2YD. The decrease in the energy gap between the quinoid state and the thermally excited biradical state results in the increase in the population of the thermally excited biradical state. Therefore, the ESR signal intensity for the solution of t-bdpi-2y is larger than that of BDPI-2Y at the same temperature. Though sufficient ESR signal can be observed for the powdered crystal of BDPI-2Y, we can detect only weak ESR signal even in the saturated solution of BDPI-2Y because of the low concentration of the ESR active radical species. In contrast to BDPI-2Y, the toluene solution of t-bdpi-2y shows relatively strong ESR signal even at 85K. This result clearly demonstrates the decrease in the energy gap between the ground quinoid state and the thermally excited biradical state of t-bdpi-2y. Unfortunately, we could not observe the zero-field splitting in the ESR spectra measured at the temperature below the melting point of toluene. rom the temperature dependence of the ESR signal in toluene solution of t-bdpi-2y (the light-irradiated solution of t-bdpi-2yd), we could evaluate the energy gap experimentally. itting the ESR signal to the Bleany-Bowers equation gave a singlet-triplet energy separation of 2.37 kcal/mol, which is slightly smaller than the theoretical value of 4.35 kcal/mol
10 igure S2. Temperature dependence of the ESR signal from the light-irradiated toluene solution of t-bdpi-2yd (1.7x10-4 M), and the toluene solution of BDPI-2Y (3.4x10-4 M). I ESR / arb.unit t-bdpi-2y BDPI-2Y temperature / K 280 The Bleany-Bowers equation used for the fitting procedure. I ESR = 3 exp ( E ST / RT ) X exp ( E ST / RT ) T
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