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Charge-Transfer Complexation Between Naphthalene Diimides and Aromatic Solvents Supporting Information

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Charge-Transfer Complexation Between Naphthalene Diimides and Aromatic Solvents Supporting Information Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is © the Owner Societies 2014 Charge-Transfer Complexation Between Naphthalene Diimides and Aromatic Solvents Supporting Information Chidambar Kulkarni,a,b Ganga Periyasamy,b S. Balasubramanianb∗ Subi J. Georgea∗1 aSupramolecular Chemistry Lab, New Chemistry Unit, Jawaharlal Nehru Center for Advanced Scientific Research (JNCASR), Bangalore-560064, India , email: [email protected] bChemistry and Physics of Materials Unit, JNCASR, Bangalore-560064 India , email: [email protected] Table of Contents 1. Experimental 2. Computational details 3. Supporting Figures 4. Computed Oscillator strengths for different complexes 5. References 1 Experimental details Electronic absorption spectra were recorded on a Perkin Elmer Lambda 900 UV-Vis-NIR spectrometer. Emission spectra were recorded on a Perkin Elmer LS 55 luminescence spectrometer. Temperature-dependent UV/Vis absorption and emission studies were performed using a Perkin Elmer LS 55 with a PTP-1 and Lambda 750 attached to PTP-1+1 Peltier system re- spectively. Jasco J-815 spectrometer was used to measuree Circular Dichro- ism (CD) spectra with a standard sensitivity (100 mdeg), scan rate of 100 nm/minute, bandwidth vaule of 1 and single accumulation for each spectra. Time-Correlated Single Photon Counting (TCSPC) experiments were per- formed using FLSP 920 spectrometer, Edinburgh Intrument. EPLED source of 380 nm was used for excitation. Unless otherwise mentioned all the optical studies were performed in 10 mm path length cuvettes. Fluorescence quan- tum yield was calculated using Quinine sulphate dihydrate as the standard with a quantum yield of 0.577 at an excitation of 350 nm using the standard formula.1 The integrated area was calculated for all spectra from 370 nm to 2 650 nm. The solvent polarity parameter ET (30) was used to analyze the influence of solvent polarity on the observed fluorescence spectral changes. 1H-NMR spectra were recorded on a Bruker AVANCE-400 spectrometer op- erating at 400 MHz at 27 ◦C. 2 Computational details Time-Dependent Density-Functional Theory (TD-DFT) studies were per- formed to understand the origin of changes observed in the experimantal UV/Vis absorption spectra of 1 and 2 in different aromatic solvents. Geom- etry optimization of model compound (1′; obtained by replacing cholesterol in 1 by methyl groups) and the complex of 1′ with four molecules of dif- ferent aromatic molecules was carried out using periodic density functional theory and the QUICKSTEP module3 as implemented in CP2K package.4 1 Combined atom centered and plane wave basis sets were used to carry out geometry optimization. BLYP exchange-correlation functional,5,6 double- zeta single polarized basis set7 and Grimme’s empirical dispersion correction (D3)8 were used for geometry optimization. Goedecker-Teter-Hutter pseu- dopotential9,10 to describe the effect of core electrons on the nuclei and an energy cut-off of 280 Ry was used. A cubical box length of 32 Awas˚ used for all the systems. LBFGS optimizer11 and Wavelet poission solver was used for all geometry optimizations. Vertical transitions were calculated on optimized geometries at B3LYP/6-31+G(d,p) level of theory for 24 states us- ing Gaussian-09.12 The molecular orbtials were visualized suing GaussView 5.0.13 2 3 Supporting Figures a) -6 3.3×10 M 1 -5 1×10 M -5 5×10 M -5 8×10 M 0.5 Normalized absorbance / a.u. 0 300 350 400 450 500 Wavelength / nm -6 1 b) 3.3×10 M -5 / a.u. 1×10 M em -5 5×10 M -5 8×10 M 0.5 λ exc = 350 nm Normalized Intensity 0 400 500 600 700 Wavelength / nm Figure S1: a) and b) Normalized UV/Vis absorption and emission spectra respectively of 1 in toluene at different concentrations 3 -6 1 5×10 M -5 1×10 M -5 5×10 M 0.5 Normalized absorbance / a.u. 0 300 350 400 450 500 Wavelength / nm Figure S2: Concentration dependent absorption spectra of 1 in mesitylene 0.06 λ coll = 540 nm 0.05 Absorption spectra -6 0.04 C=3.33×10 M 0.03 0.02 Intensity / a.u. 0.01 0 300 350 400 450 500 Wavelength / nm Figure S3: Excitation spectra of 1 in toluene overlapped with the corre- sponding UV/Vis absorption spectra (c = 3.3×10−6 M) 4 4 Benzene Toluene o-xylene 2 Mesitylene 0 CD / mdeg -2 -4 300 350 400 450 500 550 Wavelength / nm Figure S4: CD spectra of 1 in different aromatic solvents (c = 5×10−5 M) Mesitylene 520 500 480 Toluene 460 Benzene Emission maximum / nm o-DCB 440 33 34 35 36 37 38 -1 Solvent polarity ET(30) (kcalmol ) Figure S5: Variation of emission maximum of 1 versus the solvent polarity of the corresponding solvents The emission maximum red-shifts with decrease in the solvent polarity. Thus the observed spectral shifts cannot be explained based on the solvent polarity. 5 1 a) o-DCB Benzene 0.8 Toluene o-Xylene 0.6 Mesitylene -5 c = 5×10 M 0.4 Absorbance 0.2 0 300 350 400 450 500 Wavelength / nm 120 b) o-DCB Benzene / a.u. 90 Toluene em o-xylene Mesitylene 60 λ exc = 350 nm 30 Normalized Intensity 0 400 500 600 700 Wavelength / nm Figure S6: a) and b) UV/Vis absorption and emission spectra respectively of 2 in different aromatic solvents (c = 5×10−5 M) 6 Mesitylene 520 o-xylene 500 Toluene 480 460 Benzene Emission maximum / nm o-DCB 440 8.8 9 9.2 9.4 9.6 Ionization potential / eV Figure S7: Variation of emission maximum of 2 versus the ionization poten- tial of the corresponding solvents Mesitylene 520 500 480 Toluene 460 Benzene Emission maximum / nm o-DCB 440 33 34 35 36 37 38 -1 Solvent polarity ET(30) (kcalmol ) Figure S8: Variation of emission maximum of 2 versus the solvent polarity of the corresponding solvents The emission maximum red-shifts with decrease in the solvent polarity. Thus the observed shifts cannot be explained based on the solvent polarity. 7 Figure S9: Partial 1H-NMR spectra of 2 in different solvents (c = 2.5×10−3 M) 8 a) 0.8 30 °C 90 °C 0.6 0.4 Absorbance 0.2 0 300 350 400 450 500 Wavelength / nm b) 200 30 °C 90 °C 150 100 λ exc = 350 nm 50 Emission intensity / a.u. 0 400 500 600 700 Wavelength / nm Figure S10: Temperature-dependent UV/Vis absorption (a) and emission spectra (b) of 2 in o-DCB at every 10 ◦C(c=5×10−5 M) 9 a) 30 °C 0.6 90 °C 0.4 Absorbance 0.2 0 300 350 400 450 500 Wavelength / nm 250 b) 30 °C 200 90 °C 150 100 λ exc = 350 nm 50 Emission intensity / a.u. 0 400 500 600 700 Wavelength / nm Figure S11: Temperature-dependent UV/Vis absorption (a) and emission spectra (b) of 2 in mesitylene at every 10 ◦C (c = 5×10−5 M). Arrows indicates spectral changes with increase in temperature. Although the emission intensity decrease with increase in temperature, monomeric emission (at 410 nm) does not increase. This observation sug- gestions that CT complex is not dissociated at even higher temperatures. 10 2 a) o-DCB Benzene 1.5 Toluene o-Xylene Mesitylene 1 -4 c = 1×10 M Absorbance 0.5 0 300 350 400 450 500 Wavelength / nm 300 b) o-DCB 250 Benzene Toluene 200 o-Xylene Mesitylene 150 -4 c = 1×10 M 100 λ exc = 350 nm 50 Emission intensity / a.u. 0 400 500 600 700 Wavelength / nm Figure S12: a) and b) UV/Vis absorption and emission spectra of 2 respec- tively in different aromatic solvents (c = 1×10−4 M) The lack of any scattering at higher wavelengths (> 450 nm) and minimal changes in the spectral shapes when compared to spectra at lower concentra- tion suggests lack of inter-chromophoric interactions even at higher concen- trations. 11 a) Benzene 0.8 Mesitylene -5 c = 5×10 M 0.6 0.4 Absorbance 0.2 0 300 350 400 450 500 Wavelength / nm 60 b) λ Benzene ex =350 nm / a.u. λ Mesitylene ex = 350 nm em Mesitylene λ = 420 nm 40 ex 20 Normalized intensity 0 400 500 600 700 Wavelength / nm Figure S13: a) and b) UV/Vis absorption and emission spectra respectively of NDI-Amph (c = 5×10−5 M) 12 0.8 a) Benzene Mesitylene -5 0.6 c = 5×10 M 0.4 Absorbance 0.2 0 300 350 400 450 500 Wavelength / nm b) λ Benzene ex = 350 nm 10 / a.u. λ Mesitylene ex = 350 nm em λ Mesitylene ex = 420 nm 5 Normalized intensity 0 400 500 600 700 Wavelength / nm Figure S14: a) and b) UV/Vis absorption and emission spectra respectively of NDI-Bolaamph (c = 5×10−5 M) As can be seen from emission spectra, even exciting at the CT band (>400 nm) also yields similar emission features. This again suggests that the emis- sion is arising from ground-state charge-transfer (CT) 13 Molecule Fluorescence quantum yield (Φf ) in o-DCB Benzene Toluene o-Xylene Mesitylene 2 0.0067 0.0628 0.0222 0.0208 0.0100 NDI-Bolaamph 0.0040 0.0153 0.0137 0.0127 0.0072 NDI-Amph 0.0044 0.0135 0.0129 0.0138 0.0077 Table S1: Fluorescence quantum yield (Φf ) of different molecules in various aromatic solvents (c = 5×10−5 M) Generally the fluorescence intensity quenches with the formation of charges- 14 transfer complexes.
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