Graduate School of Materials Science, Nara Institute of Science and Technology, Takayama, Ikoma, Nara, , Japan.
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1 Supporting Information for Oligo- and polyfluorenes meet cellulose alkyl esters: Retention, inversion, and racemization of circularly polarized luminescence (CPL) and circular dichroism (CD) via intermolecular C-H/O=C interactions Sibo Guo, a Nozomu Suzuki, b and Michiya Fujiki a * a Graduate School of Materials Science, Nara Institute of Science and Technology, Takayama, Ikoma, Nara, , Japan b Department of Chemistry, Faculty of Science, Rikkyo University, Nishi-Ikebukuro, Toshima, Tokyo , Japan Contents 1. CD/UV-vis and CPL/PL spectra of hybridized CTA and CABu films 2. containing 9,9-dialkylfluorene oligomers and polymers (repeating number n = 1,2,3,5,7,47 (PF6), and 201 (PF8)) 1 H- and 13 C-NMR spectra in CDCl 3 and elemental analysis of CTA, CABu, and PF8 in CDCl 3 3. Computational simulation (geometry and CD/UV-vis spectra) of CTA-PF8 hybrid film with Materials Studio 4. 1D CP/MAS Solid state NMR spectra of PF8, CTA, and their hybridized PF8-CTA solids S D Solid state 1 H- 13 C HETCOR spectrum of PF8 and CTA hybridized S11 6. Calculation results for four rotamers (ID33, ID38, ID83, and ID88) of trimer with Gaussian09 7. Measurement parameters of 1D SS CP/MAS 13 C-NMR and 2D SS HETCOR 1 H-/ 13 C-NMR spectra 8. Verification of rotation angle dependent CD and CPL of hybridized CTA and CABu films with PF6 9. Comparison of three spin-coated film CD spectra of CTA, CABu, and PF6 S WAXD profiles of CTA with PF6 and CABu with PF6 on a Si substrate by drop-casted from chloroform solution in air S Added in notes in relation to experimental instructions S48 S2 S4 S8 S12 S44 S45 S1
2 6 0.5 Abs = 1/2 (Abs L + Abs R ) CTA with Monomer CTA with Dimer CTA with Trimer CTA with Pentamer CTA with Heptamer CTA with PF6 CTA with PF Wavelength (nm) 0.0 ΔAbs = (Abs L Abs R ) x 10 3 I = 1/2 (I L + I R ) CTA with Monomer CTA with Dimer CTA with Trimer CTA with Pentamer CTA with Heptamer CTA with PF6 CTA with PF ΔΙ = (I L I R ) x Wavelength (nm) Figure S1. (top) CD/UV-vis and (bottom) CPL/PL spectra of hybridized CTA and fluorene derivatives. S2
3 4 0.3 Abs = 1/2 (Abs L + Abs R ) Wavelength (nm) CABu with Monomer CABu with Dimer CABu with Trimer CABu with Pentamer CABu with Heptamer CABu with PF6 CABu with PF ΔAbs = (Abs L Abs R ) x I = 1/2 (I L + I R ) CABu with Monomer CABu with Dimer CABu with Trimer CABu with Pentamer CABu with Heptamer CABu with PF6 CABu with PF ΔΙ = (I L I R ) x Wavelength (nm) Figure S2. (top) CD/UV-vis and (bottom) CPL/PL spectra of CABu-fluorene hybrid films. S3
4 Figure S3. 1 H NMR spectrum of CTA in CDCl 3 at 25 C. Elemental analysis; Obsd C 46.80, H 5.36 (%), Calcd for [(C 12 H 16 O 8 H 2 O) n ] C 47.06, H 5.92 (%). Figure S4. 13 C NMR spectrum of CTA in CDCl 3 at 25 C. S4
5 Figure S5. 1 H NMR spectrum of CABu in CDCl 3 at 25 C. Elemental analysis; Obsd C 56.87, H 7.43 (%). Figure S6. 13 C NMR spectrum of CABu in CDCl 3 at 25 C. S5
6 Figure S7. 1 H NMR spectrum of PF8 in CDCl 3 at 25 C. Elemental analysis; Obsd C 89.63, H (%), Calcd for (C 29 H 40 ) n C 89.63, H (%). Figure S8. 13 C NMR spectrum of PF8 in CDCl 3 at 25 C. S6
7 ETERS ---) ) %], 100[%] ) LOROFORM-D -DEC :12:39 -DEC :50:16 -DEC :51: PF6-5.jdf lta ngle_pulse.exp ngle Pulse Experiment COMPLEX 384 P400 LTA_NMR 3.0 pm] [T] (400[MHz]) [s] [Hz] [kHz] LSE [MHz] ppm] 384 (Millions) 0.2[dC] [us] [s] [deg] 5[us] s] us] us] 1.0 s] X : parts per Million : 1H Figure S9. 1H NMR spectrum of PF6 in CDCl3 at 25 C. Figure S10. The potential energy surface as functions of dihedral angles, 1 and 2, of 9,9-dimethylfluorene trimer as a computational model. S7
8 400, UV-vis, (ε) / M 1 cm 1 300, , , CD, Δε / M 1 cm Wavelength (nm) Figure S11. Simulated CD and UV-vis spectra of 9,9-dimethylfluorene trimer (trimer, ID88) with a full width at half maximum of 0.10 ev Figure S12. An optimized molecular model between CTA and PF8 equilibrated at 300 K obtained with Forcite module of Materials Studio. S8
9 Table S1-1. The distances between selected C H and O=C groups for C H/O=C interactions. Distance 1 is from one proton of n-octyl groups to O=C, whilst distance 2 is from another proton to O=C by MD calculation. Group name Distance 1 (Å) Distance 2 (Å) C 9 =O/H-C a C 9 =O/H-C b C 9 =O/H-C c C 7 =O/H-C e C 11 =O/H-C e C 11 =O/H-C g Table S1-2. T The distances between selected C H and O=C groups for C H/O=C interactions. Distance 1 is from one proton of n-octyl groups to O=C, whilst distance 2 is from another proton to O=C by MD calculation. Group name Distance 1 (Å) Distance 2 (Å) C 9 =O/H-C a C 9 =O/H-C b C 9 =O/H-C c C 7 =O/H-C e C 11 =O/H-C e C 11 =O/H-C g S9
10 Figure S13. 1D CP/MAS solid state 13 C NMR spectra of CTA-PF8 hybrid (green), CTA (red), and PF8 (blue). Table S2. Chemical shifts of CTA by 1D CP/MAS solid state 13 C NMR. Group name Chemical shifts (ppm) C=O C C 2, C 3, C 4, C C S10
11 Figure S14. The solid-state 2D 1 H- 13 C HETCOR NMR spectrum of PF8 (proton pulsed, carbon-13 observed). Figure S15. The solid-state 2D 1 H- 13 C HETCOR NMR spectrum of CTA (proton pulsed, carbon-13 observed). S11
12 Figure S16. ID33: Optimized 9,9-dimethylfluorene trimer by DFT calculation. *********************************************************************** Excited states from <AA,BB:AA,BB> singles matrix: *********************************************************************** Ground to excited state transition electric dipole moments (Au): state X Y Z Dip. S. Osc Ground to excited state transition velocity dipole moments (Au): state X Y Z Dip. S. Osc S12
13 Ground to excited state transition magnetic dipole moments (Au): state X Y Z Ground to excited state transition velocity quadrupole moments (Au): state XX YY ZZ XY XZ YZ S13
14 <0 del b> * <b rxdel 0> + <0 del b> * <b delr+rdel 0> Rotatory Strengths (R) in cgs (10**-40 erg-esu-cm/gauss) state XX YY ZZ R(velocity) E-M Angle S14
15 /2[<0 r b>*<b rxdel 0> + (<0 rxdel b>*<b r 0>)*] Rotatory Strengths (R) in cgs (10**-40 erg-esu-cm/gauss) state XX YY ZZ R(length) /2[<0 del b>*<b r 0> + (<0 r b>*<b del 0>)*] (Au) state X Y Z Dip. S. Osc.(frdel) S15
16 Excitation energies and oscillator strengths: Excited State 1: Singlet-A ev nm f= <S**2>= > This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A ev nm f= <S**2>= > > Excited State 3: Singlet-A ev nm f= <S**2>= > > Excited State 4: Singlet-A ev nm f= <S**2>= > > > > > Excited State 5: Singlet-A ev nm f= <S**2>= > > > > > > > > > > > Excited State 6: Singlet-A ev nm f= <S**2>=0.000 S16
17 146 -> > > > > > Excited State 7: Singlet-A ev nm f= <S**2>= > > > > > > > > > > Excited State 8: Singlet-A ev nm f= <S**2>= > > Excited State 9: Singlet-A ev nm f= <S**2>= > > > Excited State 10: Singlet-A ev nm f= <S**2>= > > > > > > > Excited State 11: Singlet-A ev nm f= <S**2>= > > > > > > > S17
18 154 -> > Excited State 12: Singlet-A ev nm f= <S**2>= > > > > > > Excited State 13: Singlet-A ev nm f= <S**2>= > > > > > > > > > Excited State 14: Singlet-A ev nm f= <S**2>= > > > > > > > > > Excited State 15: Singlet-A ev nm f= <S**2>= > > > > > > > > > Excited State 16: Singlet-A ev nm f= <S**2>=0.000 S18
19 147 -> > > > > > Excited State 17: Singlet-A ev nm f= <S**2>= > > > Excited State 18: Singlet-A ev nm f= <S**2>= > > > > > > > Excited State 19: Singlet-A ev nm f= <S**2>= > > > > > > > > Excited State 20: Singlet-A ev nm f= <S**2>= > > > > > > > > > > S19
20 Figure S17. ID38: Optimized 9,9-dimethylfluorene trimer by DFT calculation. Excited states from <AA,BB:AA,BB> singles matrix: *********************************************************************** Ground to excited state transition electric dipole moments (Au): state X Y Z Dip. S. Osc Ground to excited state transition velocity dipole moments (Au): state X Y Z Dip. S. Osc S20
21 Ground to excited state transition magnetic dipole moments (Au): state X Y Z Ground to excited state transition velocity quadrupole moments (Au): state XX YY ZZ XY XZ YZ S21
22 <0 del b> * <b rxdel 0> + <0 del b> * <b delr+rdel 0> Rotatory Strengths (R) in cgs (10**-40 erg-esu-cm/gauss) state XX YY ZZ R(velocity) E-M Angle S22
23 /2[<0 r b>*<b rxdel 0> + (<0 rxdel b>*<b r 0>)*] Rotatory Strengths (R) in cgs (10**-40 erg-esu-cm/gauss) state XX YY ZZ R(length) /2[<0 del b>*<b r 0> + (<0 r b>*<b del 0>)*] (Au) state X Y Z Dip. S. Osc.(frdel) S23
24 Excitation energies and oscillator strengths: Excited State 1: Singlet-A ev nm f= <S**2>= > This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A ev nm f= <S**2>= > > Excited State 3: Singlet-A ev nm f= <S**2>= > > Excited State 4: Singlet-A ev nm f= <S**2>= > > > > Excited State 5: Singlet-A ev nm f= <S**2>= > > > > > > Excited State 6: Singlet-A ev nm f= <S**2>= > > > > > > Excited State 7: Singlet-A ev nm f= <S**2>=0.000 S24
25 147 -> > > > > > > Excited State 8: Singlet-A ev nm f= <S**2>= > > > Excited State 9: Singlet-A ev nm f= <S**2>= > > > > Excited State 10: Singlet-A ev nm f= <S**2>= > > > > > > Excited State 11: Singlet-A ev nm f= <S**2>= > > > > > > Excited State 12: Singlet-A ev nm f= <S**2>= > > > > > > Excited State 13: Singlet-A ev nm f= <S**2>= > > S25
26 152 -> > > > > Excited State 14: Singlet-A ev nm f= <S**2>= > > > > > > > Excited State 15: Singlet-A ev nm f= <S**2>= > > > > > Excited State 16: Singlet-A ev nm f= <S**2>= > > > > > Excited State 17: Singlet-A ev nm f= <S**2>= > > > > Excited State 18: Singlet-A ev nm f= <S**2>= > > > > > > > Excited State 19: Singlet-A ev nm f= <S**2>= > S26
27 147 -> > > > > Excited State 20: Singlet-A ev nm f= <S**2>= > > > > > Figure S18. ID83: Optimized 9,9-dimethylfluorene trimer by DFT calculation. *********************************************************************** Excited states from <AA,BB:AA,BB> singles matrix: *********************************************************************** Ground to excited state transition electric dipole moments (Au): state X Y Z Dip. S. Osc S27
28 Ground to excited state transition velocity dipole moments (Au): state X Y Z Dip. S. Osc Ground to excited state transition magnetic dipole moments (Au): state X Y Z S28
29 Ground to excited state transition velocity quadrupole moments (Au): state XX YY ZZ XY XZ YZ <0 del b> * <b rxdel 0> + <0 del b> * <b delr+rdel 0> Rotatory Strengths (R) in cgs (10**-40 erg-esu-cm/gauss) state XX YY ZZ R(velocity) E-M Angle S29
30 /2[<0 r b>*<b rxdel 0> + (<0 rxdel b>*<b r 0>)*] Rotatory Strengths (R) in cgs (10**-40 erg-esu-cm/gauss) state XX YY ZZ R(length) /2[<0 del b>*<b r 0> + (<0 r b>*<b del 0>)*] (Au) S30
31 state X Y Z Dip. S. Osc.(frdel) Excitation energies and oscillator strengths: Excited State 1: Singlet-A" ev nm f= <S**2>= > This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A' ev nm f= <S**2>= > > Excited State 3: Singlet-A' ev nm f= <S**2>= > > Excited State 4: Singlet-A" ev nm f= <S**2>= > > > > > S31
32 Excited State 5: Singlet-A" ev nm f= <S**2>= > > > > > > > > Excited State 6: Singlet-A' ev nm f= <S**2>= > > > > > > > > Excited State 7: Singlet-A" ev nm f= <S**2>= > > > > > > > Excited State 8: Singlet-A" ev nm f= <S**2>= > > Excited State 9: Singlet-A' ev nm f= <S**2>= > > > > > Excited State 10: Singlet-A' ev nm f= <S**2>= > > > > S32
33 154 -> > > Excited State 11: Singlet-A" ev nm f= <S**2>= > > > > > > Excited State 12: Singlet-A" ev nm f= <S**2>= > > > > > > Excited State 13: Singlet-A' ev nm f= <S**2>= > > > > > > > > > Excited State 14: Singlet-A" ev nm f= <S**2>= > > > > > Excited State 15: Singlet-A" ev nm f= <S**2>= > > > > > > S33
34 154 -> Excited State 16: Singlet-A' ev nm f= <S**2>= > > > > Excited State 17: Singlet-A' ev nm f= <S**2>= > > Excited State 18: Singlet-A' ev nm f= <S**2>= > > > > > > Excited State 19: Singlet-A' ev nm f= <S**2>= > > > > > > > > > > Excited State 20: Singlet-A" ev nm f= <S**2>= > > > > > S34
35 Figure S19. ID88: Optimized 9,9-dimethylfluorene trimer by DFT calculation. *********************************************************************** Excited states from <AA,BB:AA,BB> singles matrix: *********************************************************************** Ground to excited state transition electric dipole moments (Au): state X Y Z Dip. S. Osc Ground to excited state transition velocity dipole moments (Au): state X Y Z Dip. S. Osc S35
36 Ground to excited state transition magnetic dipole moments (Au): state X Y Z Ground to excited state transition velocity quadrupole moments (Au): state XX YY ZZ XY XZ YZ S36
37 <0 del b> * <b rxdel 0> + <0 del b> * <b delr+rdel 0> Rotatory Strengths (R) in cgs (10**-40 erg-esu-cm/gauss) state XX YY ZZ R(velocity) E-M Angle S37
38 /2[<0 r b>*<b rxdel 0> + (<0 rxdel b>*<b r 0>)*] Rotatory Strengths (R) in cgs (10**-40 erg-esu-cm/gauss) state XX YY ZZ R(length) /2[<0 del b>*<b r 0> + (<0 r b>*<b del 0>)*] (Au) state X Y Z Dip. S. Osc.(frdel) S38
39 Excitation energies and oscillator strengths: Excited State 1: Singlet-A ev nm f= <S**2>= > This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: Singlet-A ev nm f= <S**2>= > > Excited State 3: Singlet-A ev nm f= <S**2>= > > Excited State 4: Singlet-A ev nm f= <S**2>= > > > > > Excited State 5: Singlet-A ev nm f= <S**2>= > > > > > > > > > > > S39
40 Excited State 6: Singlet-A ev nm f= <S**2>= > > > > > > Excited State 7: Singlet-A ev nm f= <S**2>= > > > > > > > > > > Excited State 8: Singlet-A ev nm f= <S**2>= > > Excited State 9: Singlet-A ev nm f= <S**2>= > > > Excited State 10: Singlet-A ev nm f= <S**2>= > > > > > > > Excited State 11: Singlet-A ev nm f= <S**2>= > > > > > > S40
41 154 -> > > Excited State 12: Singlet-A ev nm f= <S**2>= > > > > > > Excited State 13: Singlet-A ev nm f= <S**2>= > > > > > > > > > Excited State 14: Singlet-A ev nm f= <S**2>= > > > > > > > > > Excited State 15: Singlet-A ev nm f= <S**2>= > > > > > > > > > S41
42 Excited State 16: Singlet-A ev nm f= <S**2>= > > > > > > Excited State 17: Singlet-A ev nm f= <S**2>= > > > Excited State 18: Singlet-A ev nm f= <S**2>= > > > > > > > Excited State 19: Singlet-A ev nm f= <S**2>= > > > > > > > > Excited State 20: Singlet-A ev nm f= <S**2>= > > > > > > > > > > S42
43 Figure S20. Measurement parameters of 1D SS CP/MAS 13 C-NMR spectrum. S43
44 Figure S21. Measurement parameters of PMLG 2D SS HETCOR 1 H-/ 13 C-NMR spectrum. S44
45 Abs = 1/2 (Abs L + Abs R ) (a) CTA with PF6_CD Wavelength (nm) 0 o 45 o 90 o reversal side ΔAbs = (Abs L Abs R ) x 10 3 Abs = 1/2 (Abs L + Abs R ) (c) CABu with PF6_CD Wavelength (nm) 0 o 45 o 90 o reverssal side ΔAbs = (Abs L Abs R ) x 10 3 I = 1/2 (I L + I R ) (b) CTA with PF6_CPL 0 o 45 o 90 o reversal side Wavelength (nm) ΔΙ = (I L I R ) x 10 3 I = 1/2 (I L + I R ) (d) CABu with PF6_CPL 0 o 45 o 90 o reversal side Wavelength (nm) ΔΙ = (I L I R ) x 10 3 Figure S22. Verification of rotation angle dependent CD and CPL (0, 45, 90, and its reversal side at one specific angle) of hybridized CTA and CABu films with PF6 deposited on a round-shape quartz plate by spin=coating technique. The spectra indicated that the resulting films with our methodology are in an amorphous state without anisotropic orientation, leading to no artifacts in CD and CPL spectra. Other CTA and CABu films with oligofluorenes and PF8 were confirmed this during all CD and CPL measurements. S45
46 4 1.0 Abs = 1/2 (Abs L + Abs R ) CTA CABu PF Wavelength (nm) ΔAbs = (Abs L Abs R ) x 10 3 Figure S23. Normalized CD/UV-vis spectra of CTA (red), CABu (blue), and PF6 (green) thin films deposited onto quartz by spin coating their CHCl 3 solutions. Intensity (counts) 25,000 20,000 15,000 10,000 5,000 CTA with PF6 CABu with PF6 PF Diffraction angle, 2θ (deg) Figure S24. Comparison of the WAXD profiles of PF6 (green), CTA with PF6 (red) and CABu with PF6 (blue) on a Si substrate casted from chloroform solution in air. S46
47 Table S3. The diffraction angles and d-spacing of the WAXD profiles of PF6, CTA, CABu, CAT-PF6 hybrid and CABu-PF6 hybrid samples. Sample Name 2θ (deg) d (A ) PF CABu CTA CTA with PF CABu with PF S47
48 Added in notes in relation to experimental instructions. 1. We employed systematically to search the best weightt (PF6 and PF8)/ weight (CTA/CABu) ratios ranging from 1 mg / 1mg, 1mg/2 mg, 1 mg/3 mg, 1 mg /5 mg, 1 mg /10 mg and 10 mg /1 mg, 5 mg /1 mg, 3 mg /1 mg, 2 mg /1 mg, that were commonly dissolved in 1mL of CHCl 3. We verified that the resulting induced CD spectral sign and profiles of 1 mg /10 mg / 1mL condition, in which PF6 was diluted with CTA/CABu films gave unchanged CD (sign and profiles) with UV-vis spectra. We applied the ratio of fluorene 1 mg / cellulose 1mg / chloroform 1mL to other oligofluorenes with CTA/CABu. This month, my other student in my lab reproduced and re-confirmed these CD results that were employed as one of his/her research-course training experiments. Thus we think that the external chiral/helical chemical influences led by CTA/CABu are responsible for the current chirality/helicity transfer to various fluorene derivatives. The origin of swapping CD sign in CABu may be due to the presence of bulkier n-alkyl groups and/or due to a mixture of three n-butyryl, acetyl, and unreacted OH groups. 2. It is difficult to employ the CD measurements in vacuum-uv and far-uv region of CTA/CABu dissolved in CHCl 3 as a common organic solvent due to the cut-off wavelength issue (CHCl 3 : Absorbance at 240 nm per 1 cm (and 235 nm per 0.1 cm) exceeds 1.0 (10% transmittance) to obtain a reliable CD signals. Solvent itself acts as a short-cut optical filter shorter than its unique cut-off wavelength and a long-path optical filter longer than its unique cut-off wavelength. People always have to pay attention this cutoff wavelength led by inherent absorption bands of solvents along with its optical path length. This idea is commonly shared with the reliable, reproducible measurements of UV-vis-NIR, IR, PL, CPL, PLE, and Raman spectra. 3. Flory-Huggins theory predicted that two different kinds of polymers spontaneously cause a micro-segregation that is thermodynamically stable under an equilibrium condition. However, spin-coating technique from dilute condition containing two different polymers dissolved in very volatile solvent (CHCl 3, bp 65 C) allowed us to instantly obtain thermodynamically metastable films including non-segregated polymer hybrids. This metastable film is obtainable by kinetically controlled, flash evaporation technique. Actually, PF6/PF8 and CTA/CABu in dilute CHCl 3 solution did not cause any micro-segregation and was kept as transparent homogeneous solution state by the naked eye. This means that PF6/PF8 and oligofluorenes are possible to be molecularly dispersed into CTA/CABu acting as chirality/helicity inducible hosts with help of intermolecular C-H/O=C interactions between the fluorene derivatives and the soluble cellulose. S48
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