HKUST-Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen , China
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1 Electronic Supporting Information Aggregation-Induced Emission and Photocyclization of Poly(hexaphenyl-1,3-butadiene)s Synthesized from 1+2 Polycoupling of Internal Alkynes and Arylboronic Acids Yajing Liu, a,b Jacky W. Y. Lam, a,b Xiaoyan Zheng, b Qian Peng, c Ryan T. K. Kwok, a,b Herman H. Y. Sung, b Ian, D. Williams, b and Ben Zhong Tang a,b,d * a HKUST-Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen , China b Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration & Reconstruction, Division of Life Science, Institute for Advanced Study, Institute of Molecular Functional Materials, State Key Laboratory of Molecular Neuroscience and Division of Biomedical Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China c Key Laboratory of Organic Solids, Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing , China d Guangdong Innovative Research Team, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou , China * B. Z. T. tangbenz@ust.hk Telephone: Fax:
2 Instruments Gel permeation chromatography (GPC) was performed in THF at 40 C with an elution rate of 1.0 ml min 1 on a Waters GPC system equipped with a Waters 486 UV-vis detector, a Waters 515 HPLC pump, a set of Styragel columns (HT3, HT4 and HT6; molecular weight range ), and a column temperature controller. The THF solutions of the polymers (about 2 mg ml -1 ) were filtered through a 0.45 µm PTFE filter before being injected into the GPC system. IR spectra of the films of the polymers and monomers were recorded on a Perkin-Elmer 16 PC FTIR spectrophotometer. 1 H and 13 C NMR spectra were measured on a Bruker AV 400 spectrometer in deuterated chloroform, dimethyl sulfoxide, or dichloromethane. Thermogravimetric analysis (TGA) was carried out on a TA TGA Q5000 in nitrogen at a heating rate of 10 C/min. High-resolution mass spectra (HRMS) were recorded on a GCT premier CAB048 mass spectrometer operated in MALDI-ToF mode. UV spectra were measured on a Milton Ray Spectronic 3000 Array spectrophotometer and photoluminescence (PL) spectra were recorded on a Perkin Elmer LS 55 spectrophotometer. Photopatterning was conducted in air at room temperature using 365 nm light obtained from a Spectroline ENF-280C/F UV lamp. 2
3 Figure S1. High resolution mass spectrum of 5. Table S1. Crystal data and structure refinement for 5 Empirical formula C 42 H 34 Formula weight Temperature/K (10) Crystal system monoclinic Space group P2 1 a/å (19) b/å (2) c/å (2) α/ 90 β/ (19) γ/ 90 Volume/Å (9) Z 4 ρ calc g/cm µ/mm F(000) Crystal size/mm Radiation CuKα (λ = ) 2Θ range for data collection/ to Index ranges -14 h 14, -23 k 22, -16 l 17 Reflections collected Independent reflections [R int = , R sigma = ] Data/restraints/parameters 10268/1/761 Goodness-of-fit on F Completeness to theta = % Final R indexes [I>=2σ (I)] R 1 = , wr 2 =
4 Final R indexes [all data] R 1 = , wr 2 = Largest diff. peak/hole / e Å /-0.18 Computational details All the electronic calculations in this work were mainly performed by Gaussian 09 program. 1 The geometrical structures of molecule 5 at the gas phase were fully optimized using the DFT methods at the 6-31G* basis set with B3LYP functional 2 without any symmetry constraints. Normal mode analysis was performed at the same level of theory to ensure that the optimized structures were true minima. In addition, the structural optimization and frequency calculations in THF solution were also performed at B3LYP/6-31G* level by using the polarizable continuum model (PCM) 3, with the dielectric constant of In addition, the absence of imaginary frequency for both the optimized structures at both gas phase and solution were carefully checked. Figure S2. Crystal structure of 5. 4
5 Table S2. Dihedral angles of 5 in crystal, gas and solution states dihedral angle crystal ( o ) a gas ( o ) b solution ( o ) c C01-C02-C03-C C16-C11-C01-C C02-C01-C61-C C22-C21-C02-C a Measured from single crystal X-ray diffraction analysis. b Calculated from stimulation of a single molecule of 5 in the gas phase. c Calculated from stimulation of a single molecule of 5 in tetrahydrofuran solution using functional B3LYP 2. A CH 2 B C OH B OH B-O CH 3 D Wavenumber (cm -1 ) Figure S3. IR spectra of films of (A) 1a, (B) 2a, (C) 5 and (D) P1a/2a. 5
6 ε /10 4 (mol -1 L cm -1 ) f w (vol %) Wavelength (nm) Figure S4. Absorption spectra of P3/4 in THF and THF/H 2 O mixtures with different water fractions (f w ). Solution concentration: 10 µm. 90 min * * * 75 min 60 min 45 min 30 min 0 min Chemical shift (ppm) Figure S5. 1 H NMR spectra of P1a/2a in CD 2 Cl 2 before and after UV irradiation for 0, 30, 45, 60, 75 and 90 min. The solvent peaks were marked with asterisks. 6
7 160 min 70 min 40 min 0 min Chemical shift (ppm) Figure S6. 1 H NMR spectra of P3/4 before and after UV irradiation for 0, 40, 70, and 160 min in DMSO-d 6. Figure S7. PL spectra of THF solution and THF/water mixture (1:99, v/v) of P8. Inset: fluorescent photos of (left) THF solution and (right) 99% aqueous mixture of P8 taken under 365 nm UV illumination from a hand-held UV lamp. 7
8 References (1) Gaussian 09, Revision E.01, Gaussian, Inc., Wallingford CT, (2) (a) Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys., 1993, 98, (b) Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B, 1988, 37, (3) Tomasi, J.; Mennucci, B. Cammi, R. Quantum mechanical continuum solvation models. Chem. Rev., 2015, 105,
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