Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
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1 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
2 Study of Hopping Transport in Long Oligothiophenes and Oligoselenophenes. Dependence of Reorganization Energy on Chain Length Sanjio S. Zade and Michael Bendikov* Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel S1
3 Table S1. Absolute energies of the optimized neutral oligothiophenes and oligoselenophenes. Compound Energy at B3LYP/6-31G(d) Compound Energy at B3LYP/6-31G(d) 2T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T a Se a 20Se-C2H a T a Se a 30Se-C2H a T a Se a 50Se-C2H a a Optimization was followed by single point calculations with additional keywords, scf=tight, integral(grid=ultrafine). Table S2. Absolute energies of the cation radicals of oligothiophenes and oligoselenophenes in optimized neutral geometries. a Compound Energy at B3LYP/6-31G(d) Compound Energy at B3LYP/6-31G(d) 2T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? b Se +? b 20Se +?-C2H b T +? b Se +? b 30Se +?-C2H T +? b Se +? 50Se +?-C2H a The scf=tight keyword was used in all single point reorganization energy calculations. b Additional keyword, integral(grid=ultrafine), was used. S2
4 Table S3. Absolute energies of the optimized cation radicals of oligothiophenes and oligoselenophenes. Compound Energy at B3LYP/6-31G(d) Compound Energy at B3LYP/6-31G(d) 2T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? Se +? T +? a Se +? a 20Se +?-C2H a T +? a Se +? a a T +? a Se?-C2H 50Se +?-C2H a a Optimization was followed by single point calculations with additional keywords, scf=tight, integral(grid=ultrafine). Table S4. Absolute energies of neutral oligothiophenes and oligoselenophenes in optimized cation radical geometries. a Compound Energy at B3LYP/6-31G(d) Compound Energy at B3LYP/6-31G(d) 2T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T Se T b Se b 20Se-C2H b T b Se b 30Se-C2H b T b Se-C2H b a The scf=tight keyword was used in all single point reorganization energy calculations. b Additional keyword, integral(grid=ultrafine), was used. S3
5 Table S5. Relaxation energies for neutral oligothiophenes upon moving form the cation radical-state geometry to neutral-state geometry (λ 0 ) and for the cation radical upon moving from the neutral-state geometry to the cation radical-state geometry (λ + ) and reorganization energy (λ = λ 0 + λ + ) in ev at B3LYP/6-31G(d). Compound l 0 (ev) l + (ev) l = l 0 + l + (ev) 2T T T T T T T T T T T T T T T T T Table S6. Relaxation energies for neutral oligoselenophene upon moving form the cation radical-state geometry to neutral-state geometry (λ 0 ) and for the cation radical upon moving from the neutral-state geometry to the cation radical-state geometry (λ + ) and reorganization energy (λ = λ 0 + λ + ) in ev at B3LYP/6-31G(d). Compound l 0 (ev) l + (ev) l (ev) 2Se Se Se Se Se Se Se Se Se Se Se Se Se Se Se 20Se-C2h Se 30Se-C2h Se a 50Se-C2h a Constrained C2h geometry of cation radical was used. S4
6 Table S7. Length of neutral oligothiophenes and oligoselenophenes and their cation radicals as well as total contraction of the oligothiophenes and oligoselenophenes cation radicals relative to neutral molecules at B3LYP/6-31G(d). n nt nt + (nt - nt + ) (nt - nt + )/n nse nse + (nse - nse + ) (nse - nse + )/n S5
7 bond length (Å) 1.46 a T 6T cation radical Bond number bond length (Å) 1.46 b T 20T cation radical Bond number Figure S1. BLA for (a) 6T and 6T +? and (b) 20T and 20T +?. The x-axis is the C-C bond number starting from one end of the conjugated chain. The repeating sets of three linked points represent intra-ring C-C bonds, while every fourth point on the x-axis corresponds to an interring C-C bond. The points are linked solely as a visual aid. Only half of the molecules is shown in the figures and second half is mirror image of the first half a nt nse CnT E reorg (ev) n 0.40 b l (ev) nt Y = X nse Y = X CnT Y = X+27.8 X /n Figure S2. Reorganization energies (λ = λ 0 + λ + ) of oligothiophenes (black square), oligoselenophene (red circle) and cyclic oligothiophene in anti conformation (blue triangles) versus (a) chain length, n and (b) inverse of chain length, 1/n. S6
8 0.20 l (ev) nse Y =-9.08E X+3.67 X 2 R 2 = nt Y =7.86E X+3.29 X 2 R 2 = /n Figure S3. Reorganization energies (λ = λ 0 + λ + ) of oligothiophenes and oligoselenophenes versus reciprocal of chain length at B3LYP/6-31G(d). Quadratic extrapolation of reorganization energies versus 1/n was used. 7.5 a nt Y = X-3.30 X 2 R 2 = 0.99 IP 1a (ev) nse Y = X-3.14 X 2 R 2 = /n b nt nse IP 1v (ev) /n Figure S4. (a) Adiabatic (IP 1a ) and (b) vertical ionization potential (IP 1v ) of oligothiophenes and oligoselenophenes versus reciprocal of chain length (1/n). S7
9 Cartesian coordinates for the optimized geometries 1T T T T S8
10 T T S9
11 T T S10
12 T S11
13 T S12
14 T S13
15 T S14
16 T S15
17 T S16
18 T S17
19 T S18
20 S19
21 T S20
22 S21
23 S22
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