Composed of Thiophene, Pyrrole and Methylthio
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1 upporting Information Biradical Character of Linear π-conjugated Oligomer Dications Composed of Thiophene, Pyrrole and Methylthio End nd-capping Units Tohru Nishinaga,* Masaki Tateno, Mika Fujii, Wataru Fujita, Masayoshi Takase and Masahiko Iyoda Department of Chemistry, Graduate chool of cience and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo , Japan. Fax: (+81) ; Tel: (+81) ; General 1 H and 13 C NMR spectra were recorded on JEOL JNM-270, LA-400 or L-500 instruments. Chemical shifts are reported in ppm with reference to tetramethylsilane. Preparative gel-permeation chromatography (GPC) was performed with a JAI LC-08 chromatograph equipped with JAIGEL 1H and 2H columns. Electronic spectra were recorded on a HIMADZU UV-Vis-NIR scanning spectrophotometer (Model UV-3101-PC). ER spectra were recorded on JEOL JE-RE3X instruments. Magnetic measurements of Me-9TPC 9TPC12 2+ (bcl6 )2 were carried out on a Quantum Design MPM-XL QUID magnetometer on powder samples in the temperature range from 2 K to 300 K under 5000 Oe. The molar susceptibility, χ M, was obtained from the raw magnetic data, subtracting a diamagnetic contribution of the sample in it. Elemental analyses were performed at the microanalysis laboratory of Tokyo Metropolitan University. Commercially available reagents were used as received. olvents were distilled from relevant drying agents prior to use. 1,4-Bis(2 -thienyl)-1,4-butanedione, 1 2,5-bis(2 -thienyl) -N-alkyl-pyrrole (1), 2 6TP-C 12, 2 5,5'-Dibromo-2,2'-bithiophene 3 and 5,5 -Dibromo-2,2 :5,2 -terthiophene 4 were prepared according to the literature procedures. Computational methods DFT calculations were performed with the Gaussian 03 program. 5 All geometry optimizations were carried out at the B3LYP/6 31G(d) basis set. For ntp-c 2+ 1, the total energy of the optimized structures with C 2 symmetry was found to be lower than that with C i or C s symmetry, and therefore C 2 symmetry was also applied for the geometry optimizations of Me-nTP-C inglet biradical character was estimated with the symmetry-broken UB3LYP/6 31G(d) method with a geometry optimization and the biradical index was determined on the basis of the LUMO occupation number in natural orbital analysis. Excitation energy was computed using time-dependent density functional theory (TD B3LYP) with 6-31G(d) basis set in the B3LYP optimized geometry. 1
2 ynthesis ynthesis of 2. To a THF solution (10 ml) of 1 (m = 12) (754 mg, 1.89 mmol) and TMEDA (0.30 ml, 2.0 mmol) was added n-butyllithium (1,6 M, 2.1 mmol) in hexane at 78 C under N 2. After stirring for 30 min at 78 C and ca. 5 min at rt, dimethyldisulfide (0.20 ml, 2.3 mmol) was added to the reaction mixture at 78 C. Then, after additional stirring for 10 min at 78 C, the reaction mixture was allowed to warm to rt. A standard workup using NH 4 Cl aq and dichloromethane and column chromatography (io 2 / hexane) gave 2 (m = 12) (533 mg, 1.20 mmol, 63 %) as pale yellow oil; 1 H NMR(CDCl 3 ) δ 7.31(dd, 1H), (m, 3H), 6.90(d, 1H), 6.31(dd, 2H), 4.11(t, 2H), 2.52(s, 3H), (m, 2H), (m, 18H), 0.88(t, 3H); 13 C NMR(CDCl 3 ) δ , , , , , , , , , , , , 45.22, 31.98, 31.21, 29.68, 29.68, 29.56, 29.42, 29.40, 28.97, 26.43, 22.77, 22.21, Anal. Calcd for C 25 H 35 N 3 : C, 67.36; H, 7.91; N, 3.14;, 21.58, Found: C, 67.32; H, 7.95; N, H-NMR spectrum of 2 (m = 12) N C m H 2m+1 2 m = 12 Me 2
3 13 C-NMR spectrum of 2 (m = 12) N C m H 2m+1 2 m = 12 Me ame procedure was applied for 2 (m = 6): 71% yield; colorless oil; 1 H NMR(CDCl 3 ) δ 7.32 (dd, 1H, J = 5.2, 1.2 Hz), (m, 2H), 7.04 (d, 1H, J = 3.7 Hz), 6.90 (d, 1H, J = 3.7 Hz), (m, 2H), 4.11 (t, 2H, J = 7.9 Hz), 2.53 (s, 3H), (m, 2H), (m, 6H), 0.81 (t, 3H, J = 7.2 Hz); 13 C NMR δ 137.1, 136.2, 134.6, 131.0, 128.3, 127.8, 127.0, , , 125.0, 110.7, 110.6, 45.1, 31.1, 31.0, 26.0, 22.4, 22.0, Anal. Calcd for C19H23N3: N, 3.87; C, 63.11; H, Found: N, 3.80; C, 63.43; H,
4 1 H-NMR spectrum of 2 (m = 6) N C m H 2m+1 2 m = 6 Me 13 C-NMR spectrum of 2 (m = 6) N C m H 2m+1 2 m = 6 Me 4
5 ynthesis of Me-6TP 6TP-C6. To a THF solution (30 ml) of 2 (m = 6) (1.20 g, 3.33 mmol) and TMEDA (0.60 ml, 4.0 mmol) was added n-butyllithium (1.6 M, 4.0 mmol) in hexane at 78 C under N 2. After stirring for 30 min at 78 C and 5 min at rt, CuCl 2 (1.38 g, 10.3 mmol) was added to the reaction mixture at 78 C, stirred overnight at rt. A standard workup using NH 4 Cl aq and dichloromethane and column chromatography (io 2 deactivated with 10% water / at dark / hexanedichloromethane) gave Me-6TP-C 6 (820 mg, 1.14 mmol, 68%) as yellow solid: 1 HNMR (CDCl 3 ) δ 7.14 (d, 2H, J = 3.7 Hz), 7.05 (d, 2H, J = 3.7 Hz), 6.97 (d, 2H, J = 3.7 Hz), 6.91 (d, 2H, J = 3.7 Hz), 6.36 (d, 2H, J = 3.7 Hz), 6.32 (d, 2H, J = 3.7 Hz), 4.17 (t, 4H, J = 7.8 Hz), 2.53 (s, 6H), (m, 4H), (m, 12H), 0.82 (t, 6H, J = 7.0 Hz); 13 C-NMR (CDCl3) δ 137.0, , , 133.6, 131.1, 128.4, 128.2, 126.0, 125.9, 123.6, 111.0, 110.9, 45.4, 31.20, 31.17, 26.2, 22.5, 22.2, 14.1; M(EI) m/z 720 [M + ]. Anal. Calcd for C38H44N26: N, 3.88; C, 63.29; H, Found: N, 3.89; C, 63.37; H, H-NMR spectrum of Me-6TP 6TP-C6 C 6 H 13 H 3 C N N CH 3 C 6 H 13 5
6 13 C-NMR spectrum of Me-6TP 6TP-C6 C 6 H 13 H 3 C N N CH 3 C 6 H 13 ynthesis of Me-nTP-C 12. To a THF solution (18 ml) of 2 (m = 12) (570 mg, 1.28 mmol) and TMEDA (0.19 ml, 1.27 mmol) was added n-butyllithium (1.6 M, 1.4 mmol) in hexane at 78 C under N 2. After stirring for 30 min at 78 C and 5 min at 0 C, B(O i Pr) 3 (0.35 ml, 1.5 mmol) was added to the reaction mixture at 78 C. After stirring for 90 min, pinacol (315 mg, 1.67 mmol) was added and stirred overnight at rt. A standard workup using NH 4 Cl aq and dichloromethane and column chromatography (Al 2 O 3 deactivated with 10% water / hexane-benzene) gave the boronic acid pinacol ester as pale yellow oil; 1 HNMR (CDCl 3 ): δ 7.59 (d, 1H), 7.12 (d, 1H), 7.03(d, 1H), 6.89(d, 1H), 6.36(d, 1H),6.30 (d, 1H), 4.16 (t, 3H), 2.52 (s, 3H), 1.36 (s, 12H), (m, 20H), 0.88 (t, 3H). To a mixture of the boronic acid pinacol ester prepared above (1.06 g, 1.87 mmol), 2,5-dibromo thiophene (215 mg, 0.89 mmol) and Pd (PPh 3 ) 4 (96 mg, mmol) in a tube equipped with a stop cock were added toluene (40 ml) and 2N K2CO3aq (17 ml) under N2. After heating at 110 C for 24 h, a standard workup using NH 4 Cl aq and dichloromethane, separation with preparative GPC and column chromatography (Al 2 O 3 deactivated with 10% water / hexane-benzene) and recrystallization from a mixture of dichloromethane and ethyl acetate gave Me-7TP-C 12 (258 mg, mmol, 29.8%) as yellow solid: 1 HNMR (CDCl 3 ) δ 7.14 (d, 2H), 7.09 (s, 2H), 7.04 (d, 2H), 6.96 (d, 2H), 6.91 (d, 2H), 6.36 (d, 2H), 6.32 (d, 2H), 4.17 (t, 4H), 2.53 (s, 6H), 1.61 (m, 4H), 1.20 (m, 36H), 0.87 (t, 6H); 13 CNMR (CDCl 3 ): , , , , , , , 6
7 128.20, , , , , , 45.40, 32.01, 31.21, 29.75, 29.63, 29.48, 29.45, 29.01, 26.46, 22.80, 22.21, 14.25; M(LDI-TOF) m/z [M + ]. Anal. Calcd for C 54 H 70 N 2 7 : C, 66.75; H, 7.26; N, 2.88;, 23.10, found: C, 66.53; H, 7.37; N, H-NMR spectrum of Me-7TP-C 12 H 3 C N N CH 3 C 12 H 25 C 12 H 25 7
8 13 C-NMR spectrum of Me-7TP-C 12 H 3 C N N CH 3 C 12 H 25 C 12 H 25 imilar cross-coupling of the boronic acid pinacol ester prepared above with 5,5'-Dibromo-2,2'-bithiophene gave Me-8TP-C 12 (41%) as red solid: 1 HNMR (CDCl 3 ) δ 7.14(d, 2H), 7.10(s, 4H), 7.05(d, 2H), 6.97(d, 2H), 6.91(d, 2H), 6.36(d, 2H), 6.32(d, 2H), 4.17(t, 4H), 2.53 (s, 6H), 1.61(t, 4H), 1.20 (m, 36H), 0.87(t, 6H); 13 CNMR(CDCl 3, 100MHz) δ , , , , , , , , , , , , , , , 45.39, 32.00, 31.20, 29.75, 29.63, 29.48, 29.45, 29.00, 26.44, 22.80, 22.21, 14.25; M(LDI-TOF) m/z 1052 [M + ]. Anal. Calcd for C 58 H 72 N 2 8 :C, 66.11; H, 6.89; N, 2.66;, 24.34, found:c, 65.81; H, 7.05; N,
9 1 H-NMR spectrum of Me-8TP-C 12 C 12 H 25 H 3 C N N CH 3 C 12 H C-NMR spectrum of Me-8TP-C 12 C 12 H 25 H 3 C N N CH 3 C 12 H 25 9
10 Cross-coupling with 5,5 -Dibromo-2,2 :5,2 -terthiophene gave Me-9TP-C 12 (53%) as red-brown solid: 1 HNMR (CDCl 3 ) δ 7.15 (d, 2H), 7.10 (s, br, 6H), 7.04 (d, 2H), 6.97 (d, 2H), 6.91 (d, 2H), 6.36 (d, 2H), 6.32 (d, 2H), 4.17 (t, 4H), 2.53 (s, 6H), 1.61 (m, 4H), (m, 36H), 0.87 (t, 6H); 13 CNMR(CDCl 3 ) δ , , , , , , , , , , , , , , , , , 45.38, 32.01, 31.20, 29.75, 29.63, 29.48, 29.45, 29.00, 26.44, 22.80, 22.20, 14.25; M(LDI-TOF) m/z 1135 [M + ]. Anal. Calcd for C62H74N29 :C, 65.56; H, 6.57; N, 2.47;, 25.41, found:c, 65.62; H, 6.58; N, H-NMR spectrum of Me-9TP-C 12 H 3 C N N CH 3 C 12 H 25 C 12 H 25 10
11 13 C-NMR spectrum of Me-9TP-C 12 H 3 C N N CH 3 C 12 H 25 C 12 H 25 ynthesis of 8TP-C 12. To a THF solution (8 ml) of 2 (m = 12) (582 mg, 1.33 mmol) and TMEDA (0.22 ml, 1.5 mmol) was added n-butyllithium (1.6 M, 1.5 mmol) in hexane at -78 C under N 2. After stirring for 40 min at 78 C, nme 3 Cl (1.0 M, 1.5 mmol) was added to the reaction mixture at 78 C and stirred additional 3h at rt. A standard workup using water and dichloromethane gave a crude trimethylstannane was obtained. To a mixture of the crude trimethylstannane, 5,5'-Dibromo-2,2'-bithiophene (160 mg, 0.49 mmol) and Pd (PPh 3 ) 4 (62 mg, mmol) in a tube equipped with a stop cock were added THF (20 ml) under N 2. After heating at 70 C for 3d, a standard workup using NH 4 Cl aq and dichloromethane and separation with preparative gel permeation chromatography and column chromatography (Al 2 O 3 / CHCl 3 ) gave 8TP-C 12 (124 mg, 0.13 mmol, 26 %) as orange solid: 1 HNMR(500MHz, CDCl 3 ) δ 7.32 (dd, 2H), δ7.14 (d, 2H), δ (m, 8H), δ6.97(d, 2H), δ6.38 (d, 2H), δ6.34 (d, 2H), δ4.17 (t, 4H), δ (m, 4H), δ (m, 36H), δ0.87 (t, 6H); M (MALDI-TOF) m/z 961[M + ], matrix dithranol. 11
12 1 H-NMR spectrum of 8TP-C 12 C 12 H 25 N N C 12 H 25 ynthesis of Me-nTP-C m (bcl - 6 ) 2. To a C 2 solution (12 ml) of Me-6TP-C 12 (30 mg, mmol) was slowly added bcl 5 (0.1 M, 0.12 mmol) in dichloromethane at rt under N 2. After stirring for 5 min at rt, the precipitate was collected on a filter and washed with C 2 and then with hexane gave Me-6TP-C 6 (bcl - 6 ) 2. (52 mg, mmol, 94%) as deep purple solid: Anal. Calcd for C38H44Cl12N26b2: C, 32.83; H, 3.19; N, 2.02; Cl; 30.60; ; 13.84; b; Found: C, 32.95; H, 3.28; N, Me-7TP-C 12 (bcl - 6 ) 2. (85%) as deep purple solid: Anal. Calcd for C54H70Cl12N27b2: C, 39.53; H, 4.30; N, 1.71; Cl; 25.93; ; 13.68; b; Found: C, 39.24; H, 4.30; N, Me-8TP-C 12 (bcl - 6 ) 2. (81%) as deep purple solid: Anal. Calcd for C58H72Cl12N28b2: C, 40.44; H, 4.21; N, 1.63; Cl; 24.70; ; 14.89; b; Found: C, 40.26; H, 4.15; N, Me-9TP-C 12 (bcl - 6 ) 2. (94%) as deep purple solid: Anal. Calcd for C62H74Cl12N29b2: C, 41.26; H, 4.13; N, 1.55; Cl; 23.57; ; 15.99; b; Found: C, 41.02; H, 4.04; N,
13 Ref. 1. J. Nakazaki, I. Chung, M. M. Matsushita, T. ugawara, R. Watanabe, A. Izuoka and Y. Kawada, J. Mater. Chem., 2003, 13, R. E. Niziurski-Mann and M. P. Cava, Adv. Mater., 1993, 5, P. A. Chaloner,. R. Gunatunga, and P. B. Hitchgcock, J. Chem. oc., Perkin Trans. 2, 1997, K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. oc. Jpn., 1989, 62, Gaussian 03, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. chlegel, G. E. cuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam,.. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. calmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. tratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. alvador, J. J. Dannenberg, V. G. Zakrzewski,. Dapprich, A. D. Daniels, M. C. train, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul,. Clifford, J. Cioslowski, B. B. tefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, Gaussian, Inc., Wallingford CT,
14 (a) (b) (c) Figure 1. pin distributions of the singlet biradicals of (a) 8T 2+, (b) 8TP-C 1 2+ and (c) Me-nTP-C
15 Me N R Me N R Me-6TP TP-C1 2+ Me-7TP TP-C1 2+ Me N 8 R Me N R Me-8TP TP-C1 2+ Me-9TP TP-C1 2+ (a) (b) (c) (d) singlet(r) triplet singlet(u) Figure 2. Pattern of C-C bond length alternation of (a) Me-6TP-C 2+ 1, (b) Me-7TP-C 2+ 1, (c) Me-8TP-C 2+ 1 and (d) Me-9TP-C For the numbering of bond position, see the above structures. 15
16 (a) (b) (c) (d) (e) 2e - 1e - 1e - Figure 3. Cyclic voltammogram of (a) Me-6TP-C 6, (b) Me-7TP-C 12, (c) Me-8TP-C 12 and (d) Me-9TP-C 12. (e) Linear sweep voltammetry of Me-9TP-C 12. Conditions: n-bu 4 N + PF 6 (0.1M) in dry CH 2 Cl 2 under N 2 at r.t; reference electrode: Ag/Ag + (0.01M AgNO 3 in MeCN); working electrode: glassy carbon. Potentials are referred to Fc/Fc +. 16
17 (a) (b) Figure 4. Cyclic voltamograms of (a) 6TP and (b) 8TP. Conditions: n-bu 4 N + PF 6 - (0.1M) in dry CH 2 Cl 2 under N 2 at r.t; reference electrode: Ag/Ag + (0.01M AgNO 3 in MeCN); working electrode: glassy carbon. Potentials are referred to Fc/Fc +. (a) (b) (c) (d) Figure 5. ER spectra of (a) Me-6TPC 6 2+ (bcl 6 ) 2, (b) Me-7TPC (bcl 6 ) 2, (c) Me-8TPC (bcl 6 ) 2 and (d) Me-9TPC (bcl 6 ) 2 in the solid state at rt. 17
18 χ p T / emu K mol χ p T / 10-2 emu K mol T / K T / K Figure 6. Thermal dependence of χ M T for Me-9TPC 9TPC12 2+ (bcl6 - )2; ( ) experimental χ M T data; and the fitting curve (red solid lines) are drawn using the Bleaney Bowers equation with Curie impurity term; spin contamination = 11.1 % for g = 2.00 and = 1/2, diamagnetic susceptibility = emu mol 1, and T gap = 2000 K. 18
19 Table 1. The 2 2+ (before annihilation) values for pin-unrestricted inglet tates of Me-nTP-C 1 and nt 2+. compd 2 compd 2 6T a 2+ Me-6TP-C T a 2+ Me-7TP-C T a 2+ Me-8TP-C T a 2+ Me-9TP-C a Data from Zade,..; Bendikov, M. J. Phys. Chem. B 2006, 110, Table 2. Observed and calculated (TD-B3LYP/6-31G(d)) absorption maxima with the values of absorption coefficients (ε) and oscillator strengths(f) 2+ Me-6TP-C 1 2+ Me-7TP-C 1 2+ Me-8TP-C 1 2+ Me-9TP-C 1 Observed λ max [nm](ε) 560 (19000) 965 (141000) 585 (25400) 1093 (138000) 648 (31500) 1212 (63900) 692(48900) 1275 (48900) R(2, 1) 428 (0.12) 468 (0.30) 515 (0.51) 558 (0.80) λ max [nm](f) 912 (2.91) 1041 (3.26) 1181 (3.53) 1337 (3.68) T(2, 3) 588 (0.32) 510 (0.42) 558 (0.97) 600 (1.28) λ max [nm](f) 630 (1.41) 699 (1.52) 756 (1.54) 812 (1.27) 1053 (0.76) 1201 (0.91) 1349 (1.10) 1504 (1.30) U(B) 622 (1.05) 612 (1.32) 648 (1.75) 683 (1.94) λ max [nm](f) 996 (1.62) 1137 (1.85) 1283 (1.94) 1438 (2.04) 19
20 Table 3. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
21 E(RB+HF-LYP) = hartree Table 4. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
22
23 E(UB+HF-LYP) = hartree Table 5. Cartesian Coordinate of the optimized structure for Triplet (T) 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
24
25 E(UB+HF-LYP) = hartree Table 6. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) 7TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
26 E(RB+HF-LYP) = hartree Table 7. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) 26
27 7TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
28 E(UB+HF-LYP) = hartree Table 8. Cartesian Coordinate of the optimized structure for Triplet (T) 7TP-C1 2+ at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 28
29
30 E(UB+HF-LYP) = hartree Table 9. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) 8TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
31
32 E(RB+HF-LYP) = hartree Table 10. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) 8TP-C1 2+ at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 32
33
34 E(UB+HF-LYP) = hartree Table 11. Cartesian Coordinate of the optimized structure for Triplet (T) 8TP-C1 2+ at the B3LYP/6-31G(d) level. 34
35 Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
36 E(UB+HF-LYP) = hartree 36
37 Table 12. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) 9TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
38
39 E(RB+HF-LYP) = hartree Table 13. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) 9TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
40
41 E(UB+HF-LYP) = hartree Table 14. Cartesian Coordinate of the optimized structure for Triplet (T) 9TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
42
43 E(UB+HF-LYP) = hartree Table 15. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) Me-6TP 6TP-C1 2+ at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 43
44
45 E(RB+HF-LYP) = hartree Table 16. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) Me-6TP 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
46
47 E(UB+HF-LYP) = hartree Table 17. Cartesian Coordinate of the optimized structure for Triplet (T) Me-6TP 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
48
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