# Fileset

[Revised_SI.pdf](https://mdr.nims.go.jp/filesets/7eaf85c4-c61e-4d8a-9322-fe251bb3eba6/download)

## Creator

Nao Suzuki, Ziwei Hu, Sota Nakayama, Soh Kushida, Yohei Yamamoto, Wijak Yospanya, Reiko Oda, Takaki Kanbara, Junpei Kuwabara

## Rights

[Creative Commons BY-NC Attribution-NonCommercial 4.0 International](https://creativecommons.org/licenses/by-nc/4.0/)

## Other metadata

[Reproducible Chiroptical Activity from Aggregated Chiral Thienopyrroledione–Fluorene π‑Conjugated Polymers.](https://mdr.nims.go.jp/datasets/43426c5f-3588-4ddd-8929-e6f61618f3c8)

## Fulltext

Microsoft Word - Revised_SI.docx1  Supporting information  Reproducible chiroptical activity from aggregated chiral thienopyrroledione–fluorene π‑conjugated polymers.  Nao Suzuki,a Ziwei Hu,a Sota Nakayama,a Soh Kushida,a Yohei Yamamoto,a,b Wijak Yospanya,c Reiko Oda,d,c Takaki Kanbara,a Junpei Kuwabaraa,b *  a Institute of Pure and Applied Sciences, University of Tsukuba 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan. b Tsukuba Research Center for Energy Materials Science (TREMS), Institute of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan. c Advanced Institute for Materials Research (AIMR), Tohoku University, 2-1-1 Katahira, Aoba, Sendai, Miyagi, Japan d University of Bordeaux, CNRS, Bordeaux INP, CBMN, UMR 5248, F-33600 Pessac, France  E-mail: kuwabara@ims.tsukuba.ac.jp     2   Figure S1. (a) 1H NMR (CDCl3, 600 MHz, r.t.) and (b) 13C{1H} NMR spectrum of (R)-TPD (CDCl3, 150 MHz, r.t.).  3   Figure S2. 1H NMR spectrum of (R)-TPD (CDCl3, 600 MHz, r.t., 0.6-2.4 ppm)    Figure S3. 1H-1H COSY spectrum of (R)-TPD (CDCl3, 600 MHz, r.t., 0.6-2.4 ppm).   4   Figure S4. (a) 1H NMR (CDCl3, 600 MHz, r.t.) and (b) 13C{1H} NMR spectra of (R)-PFTPD (CDCl3, 150 MHz, r.t.).  5    Figure S5. MALDI-TOF-MS spectrum of (R)-PFTPD.  6   Figure S6. (a) 1H NMR (CDCl3, 600 MHz, r.t.) and (b) 13C{1H} NMR spectra of (S)-TPD (CDCl3, 150 MHz, r.t.). 7   Figure S7. (a) 1H NMR (CDCl3, 600 MHz, r.t.) and (b) 13C{1H} NMR spectra of (S)-PFTPD (CDCl3, 150 MHz, r.t.). 8    Figure S8. MALDI-TOF-MS spectrum of (S)-PFTPD.   9   Figure S9. X-ray diffraction (XRD) patterns of a cast film of (R)-PFTPD measured using CuKα radiation at room temperature.    Figure S10. DSC thermograms of (R)-PFTPD measured under an Ar atmosphere at a heating rate of 10 K min⁻¹ using a sample mass of 4.43 mg. The second heating scan after erasing the thermal history is shown.  10   Figure S11. UV-Vis absorption and photoluminescence spectra of (R)-PFTPD (a) in solution state (CHCl3, 5.0 × 10-6 M) and (b) in thin film state.  11   Figure S12. Frontier molecular orbitals (HOMO and LUMO), along with the predicted absorption wavelengths and corresponding oscillator strengths (f) obtained from a TD‑DFT calculation.  12    Figure S13. (a) UV–Vis absorption, (b) CD spectra of (R)-TPD, (c) UV–Vis absorption, and (d) CD spectra of (R)-PFTPD recorded in CHCl3 (3.0 × 10−5 M).          13    Figure S14. Photographs of (R)-PFTPD in the different solvent mixtures under natural light and under UV light (365 nm) illumination.    Figure S15. CD spectra of (S)-PFTPD aggregates prepared under different mixing conditions: (a) Condition 1 and (b) Condition 4. Figure (a) corresponds to the sample listed as Entry 2 in Table S1, while figure (b) corresponds to the sample listed as Entry 30 in Table S1. The spectra were recorded for samples of (S)-PFTPD in CHCl3/1-butanol mixtures with a volume ratio of 40:60 (3.0 × 10−5 M).   14   Figure S16. UV-Vis absorption spectra, CD spectra, and gabs factors of (R)-PFTPD (red) and (S)-PFTPD (blue) recorded in CHCl3/1-butanol mixtures with volume ratios of 40:60 (3.0 × 10−5 M).  15    Figure S17. CD spectra of (R)-PFTPD (red) and (S)-PFTPD (blue) recorded in CHCl3/1-butanol mixtures with volume ratios of 50:50, 40:60, and 30:70 (3.0 × 10−5 M). 16  Table S1. Original gabs values corresponding to the preparation conditions. a Entry Condition R or S gabs f 1 1 b S 0.0000874 2  S 0.00266 3 2 c S 0.00595 4  S 0.00231 5  S 0.0165 6  S 0.0128 7  S 0.00343 8  R −0.00513 9  R −0.00349 10 3 d S 0.0186 11  S 0.0173 12  S 0.0127 13  S 0.0151 14  S 0.0277 15  S 0.0202 16  S 0.0234 17  S 0.0158 18  S 0.00935 19  R −0.00540 20  R −0.00770 21  R −0.0188 22  R −0.0152 23  R −0.0127 24  R −0.0100 25  R −0.0118 26 4 e S 0.0114 27  S 0.0116 28  S 0.0132 29  S 0.0142 30  S 0.0181 31  R −0.0150 32  R −0.0190 33  R −0.0153 34  R −0.0175 17  a 1‑BuOH (6 mL) was added to a 75 μM solution of (R)-PFTPD or (S)-PFTPD in CHCl3 (4 mL). The conditions are shown in Table 2.  b 1‑Butanol was slowly poured into the polymer solution in CHCl3, allowing the two solvents to diffuse gradually into each other. c 1‑Butanol was added all at once to the polymer solution in CHC3, followed by manual shaking to promote immediate mixing. d 1‑Butanol was added dropwise to the polymer solution in CHCl3 under stirring. e 1‑Butanol was added dropwise to the polymer solution in CHCl3 under stirring (450 rpm). f gabs values at the peak wavelengths around 480 nm.   Table S2. Representative gabs values of (R)-PFTPD. a       a gabs values calculated from the data shown in Figures 3 and S11.   Table S3. Original glum values. a R or S glum S 0.0239 S 0.0190 S 0.0127 R −0.0256 R −0.0168 R −0.0158 a glum values (R)-PFTPD and (S)-PFTPD recorded in CHCl3/1-butanol mixtures with volume ratios of 40:60 (3×10−5 M, λex = 400 nm). Solvent ratio CHCl3 : 1-butanol gabs Wavelength 100 : 0 ~ 0 - 50 : 50 −4.2 × 10−4 485 40 : 60 −1.6 × 10−2 491 30 : 70 −6.8 × 10−3 513