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1 Supporting Information Axially Assembled Photosynthetic Antenna-Reaction Center Mimics composed of Bodipy Chromophores, Aluminum Porphyrin and Fullerene Derivatives Anthi Bagaki, a Habtom B. Gobeze, b Georgios Charalambidis, a Asterios Charisiadis, a Christina Stangel, a,c Vasilis Nikolaou, a Anastasios Stergiou, c Nikos Tagmatarchis, c, * Francis D Souza, b, * Athanassios G. Coutsolelos a, * a Department of Chemistry, University of Crete, Laboratory of Bioinorganic Chemistry, Voutes Campus, Heraklion, Crete, Greece, acoutsol@uoc.gr b Department of Chemistry, University of North Texas, 1155 Union Circle, #305070, Denton, TX , USA; Francis.DSouza@UNT.edu; c Theoretical and Physical Chemistry Institute, National Hellenic Research Foundation; 48 Vassileos Contantinou Avenue, Athens 11635, Greece. Tel.: ; tagmatar@eie.gr These authors have equally contributed. Corresponding Authors acoutsol@uoc.gr (A.G.C.); Francis.DSouza@UNT.edu (F. D.); tagmatar@eie.gr (N. T.)
2 Figure S1. Steady-state absorption spectra of toluene solutions containing 1.0 x 10-6 M BDP-O-AlTPP and and increasing amounts of C 60 -PPV-pyr. The Figure inset is a Benesi-Hildebrand plot constructed for evaluating the binding constant. Figure S2. Steady-state absorption spectra of toluene solutions containing 1.0 x 10-6 M BDP-COOO-AlTPP and increasing amounts of C 60 -pyr. The Figure inset is a Benesi-Hildebrand plot constructed for evaluating the binding constant.
3 Figure S3. Steady-state absorption spectra of toluene solutions containing 1.0 x 10-6 M BDP-COO-AlTPP and increasing amounts of C 60 -pyr. The Figure inset is a Benesi-Hildebrand plot constructed for evaluating the binding constant. (a) BDP-COO-AlTPP Ph-COO-AlTPP (b) BDP-O-AlTPP Ph-O-AlTPP Emission (a.u) Emission (a.u) Wavelength (nm) Wavelength (nm) Figure S4. Room temperature emission spectra of isoabsorbing (A = 0.1) toluene solutions of (a) BDP-COO-AlTPP and Ph-COO-AlTPP and (b) BDP-O-AlTPP and Ph-O-AlTPP. The excitation wavelength was at 546 nm where only the Al-porphyrin absorbs.
4 (a) 1.0 BDP-COO-AlTPP (b) 1.0 BDP-O-AlTPP Normalized Intensity Normalized Intensity Wavelength (nm) Wavelength (nm) Figure S5. Room temperature normalized excitation spectra of (a) BDP-COO- AlTPP and (b) BDP-O-AlTPP in dry toluene solutions monitoring the fluorescence of porphyrin at 660 nm. Fluorescence Intensity (a.u.) Wavelength (nm) Figure S6. Corresponding fluorescence spectra of toluene solutions containing 1.0 x 10-6 M BDP-COO-AlTPP upon increasing additions of C 60 -pyr upon photoexcitation at 546 nm.
5 Fluorescence Intensity (a.u.) Figure S7. Corresponding fluorescence spectra of toluene solutions containing 1.0 x 10-6 M BDP-O-AlTPP upon increasing additions of C 60 -PPV-pyr upon photoexcitation at 546 nm Wavelength (nm) 150 Fluorescence Intensity (a.u.) Wavelength (nm) Figure S8. (a) Corresponding fluorescence spectra of toluene solutions containing 1.0 x 10-6 M BDP-O-AlTPP upon increasing additions of C 60 -pyr upon photoexcitation at 546 nm.
6 Figure S9. Different view perspective of the gas phase geometry optimized structures of BDP-COO-AlTPP C 60 -PPV-pyr, BDP-COO-AlTPP C 60 -pyr, (upper part) and BDP-O-AlTPP C 60 -PPV-pyr, BDP-O-AlTPP C 60 -pyr (lower part) with the corresponding angles between the bodipy unit and the porphyrin ring.
7 Figure S10. Frontier molecular orbitals of BDP-COO-AlTPP C 60 -PPV-pyr with the corresponding energy levels. Figure S11. Frontier molecular orbitals of BDP-COO-AlTPP C 60 -pyr with the corresponding energy levels.
8 Figure S12. Frontier molecular orbitals of BDP-O-AlTPP C 60 -PPV-pyr with the corresponding energy levels. Figure S13. Frontier molecular orbitals of BDP-O-AlTPP C 60 -pyr with the corresponding energy levels.
9 Table S1. Coordinates of gas phase geometry optimized structure of BDP-COO- AlTPP C 60 -PPV-pyr calculated by DFT at the B3LYP / 6-31G(d) level. E= Hartree / particle. x y z C C C N C C C C N C C C C C N C C C C C N C C
10 C C C C C C C C C C C C C C C C C C C C C C C C C Al
11 C C C N C C C C C N C C C C C C C C C C C B F F O N
12 C C C C C C C N C C C C C C C C C C C C C C C C C C
13 C C C C C C C C C C C C C C C C C C C C C C C C C C
14 C C C C C C C C C C C C C C C C C C C C C C C C C O
15 O C C C C C C C C C C C C C C C C C C C C C C C C H
16 H H H H H H H H H H H H H H H H H H H H H H H H H H
17 H H H H H H H H H H H H H H H H H H H H H H H H H H
18 H H H H H H H H H H H H H H H H H H H H H H H H H H
19 H H H H H H H H H H H H H H H H H H H H H H H H H H
20 H H H H H C O Table S2. Coordinates of gas phase geometry optimized structure of BDP-COO- AlTPP C 60 -pyr calculated by DFT at the B3LYP / 6-31G(d) level. E= Hartree / particle. x y z C C C N C C C C N C C C C C N
21 C C C C C N C C C C C C C C C C C C C C C C C C C C
22 C C C C C C C Al C C C N C C C C C N C C C C C C C C
23 C C C B F F O N C C C C C C C N C C C C C C C C C C
24 C C C C C C C C C C C C C C C C C C C C C C C C C C
25 C C C C C C C C C C C C C C C C C C C C C C C C C C
26 O H H H H H H H H H H H H H H H H H H H H H H H H H
27 H H H H H H H H H H H H H H H H H H H H H H H H H H
28 H H H H H Table S3. Coordinates of gas phase geometry optimized structure of BDP-O- AlTPP C 60 -PPV-pyr calculated by DFT at the B3LYP / 6-31G(d) level. E= Hartree / particle. x y z C C C N C C C C N C C C C C N C
29 C C C C N C C C C C C C C C C C C C C C C C C C C C
30 C C C C C C Al C C C N C C C C C N C C C C C C C C C
31 C C B F F O N C C C C C C C N C C C C C C C C C C C
32 C C C C C C C C C C C C C C C C C C C C C C C C C C
33 C C C C C C C C C C C C C C C C C C C C C C C C C C
34 C C C C C C O O C C C C C C C C C C C C C C C C C C
35 C C C C C C H H H H H H H H H H H H H H H H H H H H
36 H H H H H H H H H H H H H H H H H H H H H H H H H H
37 H H H H H H H H H H H H H H H H H H H H H H H H H H
38 H H H H H H H H H H H H H H H H H H H H H H H H H H
39 H H H H H H H H H H H H Table S4. Coordinates of gas phase geometry optimized structure of BDP-O- AlTPP C 60 -pyr calculated by DFT at the B3LYP / 6-31G(d) level. E= Hartree / particle. x y z C C C N C C C C N C
40 C C C C N C C C C C N C C C C C C C C C C C C C C C
41 C C C C C C C C C C C C Al C C C N C C C C C N C C C
42 C C C C C C C C B F F O N C C C C C C C N C C C C C
43 C C C C C C C C C C C C C C C C C C C C C C C C C C
44 C C C C C C C C C C C C C C C C C C C C C C C C C C
45 C C C C H H H H H H H H H H H H H H H H H H H H H H
46 H H H H H H H H H H H H H H H H H H H H H H H H H H
47 H H H H H H H H Table S5: DFT calculated properties of BDP-COO-AlTPP C 60 -PPV-pyr, BDP- COO-AlTPP C 60 -pyr, BDP-O-AlTPP C 60 -PPV-pyr and BDP-O-AlTPP C 60 -pyr: HOMO and LUMO energies and HOMO-LUMO gap (HL). Compound HOMO (ev) LUMO (ev) HL (ev) BDP-COO-AlTPP C 60 -PPV-pyr BDP-COO-AlTPP C 60 -pyr BDP-O-AlTPP C 60 -PPV-pyr BDP-O-AlTPP C 60 -pyr
48 Figure S14. 1 H NMR spectrum of compound BDP-O-AlTPP in CDCl 3. Figure S15. 1 H NMR spectrum of compound Ph-O-AlTPP in CDCl 3.
49 Figure S16. 1 H NMR spectrum of compound BDP-COO-AlTPP in CDCl 3. Figure S17. 1 H NMR spectrum of compound Ph-COO-AlTPP in CDCl 3.
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