Contents: Cartesian coordinates of DFT optimized [B3LYP 6 31G+(d)] structures of reduced model ethynyl dithiaporphyrins 3a and 3b 16
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1 Supporting Information: Pi Extended Ethynyl 21,23 Dithiaporphyrins: A Synthesis and Comparative Study of Electrochemical, Optical and Self Assembling Properties Ashley D. Bromby; Samantha N. Keller; Kevin J. A. Bozek; Vance E. Williams; Todd C. Sutherland* *Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary Alberta, Canada Fax: ;Tel: ;E mail: todd.sutherland@ucalgary.ca Contents: Compound characterization 1 H and 13 C NMR 1 Scheme S1: Synthesis of ethynyl precursors 1a/b 12 Figure S1: Differential pulse voltammograms for dithiaporphyrins 3a and 3b 13 Figure S2: Frontier molecular orbitals of dithiaporphyrins 3a, 3b and N 2 S 2 TPOC Table S1: Oscillator strengths and peak widths at full height half maximum for compounds 3a and 3b 14 Figure S3: DSC thermogram of dithiaporphyrin 3b 15 Figure S4: Powder XRD of porphyrin 3a 15 Figure S5: Powder XRD of blank capillary tube 16 Cartesian coordinates of DFT optimized [B3LYP 6 31G+(d)] structures of reduced model ethynyl dithiaporphyrins 3a and 3b 16
2 1 1 Bromo 4 (dodecyloxy)benzene 4a Bromo 4 (dodecyloxy)benzene 4a
3 2 4 Dodecyloxy[(trimethylsilyl)ethynyl]benzene 5a ppm Dodecyloxy[(trimethylsilyl)ethynyl]benzene 5a
4 3 4 Dodecyloxyethynylbenzene 1a ppm Dodecyloxyethynylbenzene 1a ppm
5 4 2,5 Bis[(4 dodecyloxyethynylphenyl)hydroxymethyl]thiophene 2a ppm ,5 Bis[(4 dodecyloxyethynylphenyl)hydroxymethyl]thiophene 2a ppm
6 5 5, 10, 15, 20 Tetra(4 dodecyloxyethynylphenyl) 21, 23 dithiaporphyrin 3a 5, 10, 15, 20 Tetra(4 dodecyloxyethynylphenyl) 21, 23 dithiaporphyrin 3a
7 6 4 Bromododecanoylbenzene 1 Bromo 4 dodecylbenzene 4b
8 7 1 Bromo 4 dodecylbenzene 4b 4 Dodecyl[(trimethylsilyl)ethynyl]benzene 5b
9 8 4 Dodecyl[(trimethylsilyl)ethynyl]benzene 5b 4 Dodecylethynylbenzene 1b
10 9 4 Dodecylethynylbenzene 1b 2,5 Bis[(4 dodecylethynylphenyl)hydroxymethyl]thiophene 2b
11 10 2,5 Bis[(4 dodecylethynylphenyl)hydroxymethyl]thiophene 2b 5, 10, 15, 20 Tetra(4 dodecylethynylphenyl) 21, 23 dithiaporphyrin 3b
12 11 5, 10, 15, 20 Tetra(4 dodecylethynylphenyl) 21, 23 dithiaporphyrin 3b 2, 5 thiophenedicarboxaldehyde 2, 5 thiophenedicarboxaldehyde
13 12 Br BrC 12 H 25 OH K 2 CO 3,KI 90% O Br OC 12 H 25 4a SiMe 3 Me 3 Si OC 12 H 25 Br Cl C 11 H 23 AlCl 3 40% Br 58% C 11 H 23 O H 2 N NH 2 KOH Pd(PPh 3 ) 2 Cl 2 5a, 62% CuI, PPh 3 NEt Me C 3 3 Si 12 H 25 5b, 48% Br C 12 H 25 4b Scheme S1: Synthesis of ethynyl precursors 1a/b.
14 13 Figure S1: Differential pulse voltammograms for dithiaporphyrins 3a (left) and 3b (right) at 100 mv s 1.
15 14 Figure S2: Frontier molecular orbitals of dithiaporphyrins 3a, 3b and N 2 S 2 TPOC 12 using DFT methods at the B3LYP/6 31G(+)d level. Note: Orbital pictures are LUMO+1, LUMO, HOMO and HOMO 1 from top to bottom and the HOMO 2 orbital is not shown. Table S2: Oscillator strengths and peak widths at full height half maximum for compounds 3a and 3b. Compound Soret QIV QIII QII QI 3a 0.72 (1226)* 0.10 (1461) 0.20 (835) (586) 0.03 (562) 0.14 (527)* 3b 0.96 (1095) 0.09 (1294) 0.21 (777) (439) 0.03 (495) N 2 S 2 TPOC (776) 0.09 (686) 0.08 (883) (584) 0.03 (551) Note: Peak widths are reported in parentheses at full width half maximum in cm 1. Spectra of 3a and 3b were recorded in methylene chloride and N 2 S 2 TPOC 12 was recorded in toluene.*indicates oscillator strengths of both Soret bands.
16 15 Figure S3: DSC thermogram of dithiaporphyrin 3b at 5 C/min. Figure S4: Powder XRD of porphyrin 3a taken at left) room temperature right) 260 C. Inset shows smaller intensity peaks.
17 16 Figure S5: Powder XRD of blank capillary tube. Cartesian coordinates of DFT optimized [B3LYP 6 31G+(d)] structures of reduced model ethynyl dithiaporphyrins Reduced model of 3a: Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
18
19 Energy = a.u.
20 19 Reduced model of 3b: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
21
22 Energy = a.u.
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