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1 Supporting Information Ultrafast Electron Transfer from Upper Excited State of Encapsulated Azulenes to Acceptors Across an Organic Molecular Wall A. Mohan Raj, 1 Mintu Porel, 1 Puspal Mukherjee, Xiuyuan Ma, 3 Rajib Choudhury, Elena Galoppini, 3, * Pratik Sen, * and V. Ramamurthy 1, * 1 Department of Chemistry, University of Miami, Coral Gables, FL 3316, USA Department of Chemistry, Indian Institute of Technology, Kanpur, 816, India 3 Chemistry Department, Rutgers University, Newark, NJ 71, USA Department of Physical Sciences, Arkansas Tech University, Russellville, AR 781, USA Contents Page Figure S1. 1 H NMR titration spectra of Az with OA S Figure S. 1 H NMR titration spectra of GAz with OA S3 Figure S3. 1 H NMR spectra of + MV + + CB-7 S Figure S. D-DOSY spectrum of S5 Figure S5. D-DOSY spectrum of GAz@OA S6 Figure S6. Absorption and emission spectra of GAz@OA S7 Figure S7. Fluorescence titration and recovery spectra of + Py + + CB-7 S7 Figure S8. Fluorescence titration spectra of GAz@OA with MV +, MePy + and Py + S8 Figure S9. Fluorescence recovery spectra of GAz@OA with MV +, MePy + and S9 Py + with CB-7 Figure S1. Femtosecond TA spectrum of GAz@OA with MV S1 Figure S11. Fluorescence spectra of and GAz@OA at different ph. S1 Figure S1. FT-IR-ATR spectra of and GAz@OA on a) TiO and b) S11 ZrO film Figure S13. FT-IR-ATR spectra of OA solid and OA@TiO film S11 Figure S1. Orientation of GAz inside OA by MD simulation S1 Figure S15. Orientation of Az inside OA by MD simulation S13,S1 S1
2 i) a b c d e f g h i j ii) iii) iv) a b c d e f g h Figure S1. 1 H NMR (5 MHz) spectra of (i) OA( [OA] = 1 mm) in 1 mm Na B O 7 buffer/d O; (ii) Az@OA ([OA] = 1 mm), [Az] =.5 mm); (iii) Az@OA ([OA] = 1 mm), [Az] =.5 mm); (iv) Az@OA ([OA] = 1 mm), [Az] = 1 mm) in 1 mm Na B O 7 buffer/d O; represent the residual D O. S
3 i) a b c d e f g h i j ii) * * * iii) * * * Figure S. 1 H NMR (5 MHz) spectra of (i) OA( [OA] = 1 mm); (ii) GAz@OA ([OA] = 1 mm), [GAz] =.5 mm (iii) GAz@OA ([OA] = 1 mm), [GAz] =.5 mm) in 1 mm Na B O 7 buffer/d O; * and represent the bound Guiazulene protons and the residual D O respectively. S3
4 i) ii) iii) iv) Figure S3. 1 H NMR (5 MHz) spectra of (i) OA( [OA] = 1 mm) (ii) ([OA] = 1 mm), [Az] = 1 mm) ; (iii + MV + ([OA] = 1 mm), [Az] = 1 mm, [MV + ] = 1 mm) ; (iv) + MV + + CB[7] ([OA] = 1 mm), [Az] = 1 mm, [MV + ] = 1 mm, [CB-7] = 3 mm) in 1 mm Na B O 7 buffer/d O; OA, MV + and host CB-7 protons respectively. represent residual D O, host S
5 Figure S. D DOSY (5 MHz, D O) spectra of ; [OA] = 1 mm, [Az] = 1 mm in borate buffer, diffusion constant of is 1.8 x 1-6 cm /s. ; represents the shifted host protons. S5
6 * * * Figure S5. D DOSY (5 MHz, D O) spectra of GuAz@OA ; [OA] = 1 mm, [GAz] =.5 mm, diffusion constant of GuAz@OA is 1.5 x 1-6 cm /s.; and * represent the host and bound guaiazulene protons respectively. S6
7 Absorbance a b Intensity ( a.u ) Figure S6 a) Absorption spectrum of GAz@OA, [OA] = 1 x 1 - M, [GAz] =.5 x 1 - M b) Fluorescence spectrum of GAz@OA [OA] = x 1-5 M, [GAz] = 1 x 1-5 M in borate buffer (λ exc = 35 nm). 3 1 a) b) [Py + ] Py + Py Figure S7. a) Fluorescence titration spectra of with Py +, [OA] = x 1-5 M, [Az] = x 1-5 M, [Py + ] = to 7.5 x 1-5 M; b) Fluorescence recovery spectra of [OA] = x 1-5 M, [Az] = x 1-5 M, [Py + ] = 6 x 1 - M, CB[7] = 1 mm. λexc = 3 nm. S7
8 a) [MV + ] GAz@OA b) GAz@OA [MePy + ] c) GAz@OA [Py + ] Figure S8. a) Fluorescence titration spectra of GAz@OA with MV +, [OA] = x 1-5 M, [GAz] = x 1-5 M, [MV + ] = to 3.5 x 1-5 M ; b) Fluorescence titration spectra of GAz@OA with MePy +,[OA] = x 1-5 M, [GAz] = x 1-5 M,[MePy + ] = to 5 x 1-5 M; c) Fluorescence titration spectra of GAz@OA with Py +,[OA] = x 1-5 M, [GAz] = x 1-5 M,[Py + ] = to.8 x 1-5 M; λexc = 35 nm. S8
9 3 1 a) GAz@OA GAz@OA + MV GAz@OA + MV b) GAz@OA GAz@OA + MePy GAz@OA +MePy c) GAz@OA 3 1 GAz@OA + Py GAz@OA + Py Figure S9. a) Fluorescence recovery spectra of GAz@OA [OA] = 1 x 1 - M, [GAz] = 5 x 1-5 M, [MV + ] = 3 x 1 - M, CB[7] = 1 mm; b) Fluorescence recovery spectra of GAz@OA [OA] = 1 x 1 - M, [GAz] = 5 x 1-5 M, [MePy + ] = 6 x 1 - M, CB[7] = 1 mm; c) Fluorescence recovery spectra of GAz@OA [OA] = 1 x 1 - M, [GAz] = 5 x 1-5 M, [Py + ] = 6 x 1 - M, CB[7] = 1 mm; λexc = 35 nm. S9
10 a) b) Figure S1. a) Femtosecond transient absorption spectra for with 1 mm MV + at different times λ exc = nm.; b) Global fitting for wavelength range from 56 to 6 nm. 7 a) 5 b) ph ph 8.9 GAz@OA 5 ph 7. ph Figure S11. a) Fluorescence spectra of Az@OA at ph-8.9 and ph-7., [OA] = x 1-5 M, [Az] = x 1-5 M; b) Fluorescence spectra of GAz@OA at ph-8.9 and ph-7., [OA] = x 1-5 M, [GAz] = x 1-5 M. S1
11 Absorbance ( 1-3 ) a) on TiO film Absorbance ( 1-3 ) b) on ZrO film Wavenumber (cm -1 ) Wavenumber (cm -1 ) Absorbance ( 1-3 ) c) GAz@OA on TiO film Wavenumber (cm -1 ) Absorbance ( 1-3 ) d) GAz@OA on ZrO film Wavenumber (cm -1 ) Figure S1. a) FT-IR-ATR spectra of on a) TiO and b) ZrO film ; b) FT-IR-ATR spectra of GAz@OA on c) TiO and d) ZrO film. A a) b) 8 OA solid A OA@TiO film Wavenumbers (cm -1 ) Wavenumbers (cm -1 ) Figure S13. a) FT-IR-ATR spectra of OA solid; b) OA@TiO film. S11
12 Figure S1. Two different starting orientations of GAz used for 1 ns atomistic MD simulations. S1
13 S13
14 Figure S15. Three different starting orientations of Az used for 1 ns atomistic MD simulations. S1
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