Controlling Growth of Molecular Crystal Aggregates with Distinct Linear and Nonlinear Optical Properties
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1 Supporting Information Controlling Growth of Molecular Crystal Aggregates with Distinct Linear and Nonlinear Optical Properties Yusen Luo,,,# Chunqing Yuan,,# Jialiang Xu*, Yongjun Li*, Huibiao Liu, Sergey Semin, & Theo Rasing, & Wensheng Yang *, and Yuliang Li Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Organic Solids, Institute of Chemistry, CAS Research/Education Center for Excellence in Molecular Sciences, Chinese Academy of Sciences, Beijing , P. R. China. State Key Laboratory for Supramolecular Structures and Materials, College of Chemistry, Jilin University, Changchun , P. R. China. School of Chemical Engineering and Technology, Tianjin University, Yaguan Road 135, Tianjin , P. R. China. & Radboud University, Institute for Molecules and Materials (IMM), Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands. # These authors contribute equally. Corresponding Authors: jialiang.xu@tju.edu.cn, liyj@iccas.ac.cn, wsyang@jlu. edu.cn S-1
2 Materials. All chemical reagents were purchased from Alfa Aesar or Aldrich Chemicals and used without further purification. Column chromatography was performed on silica gel (size mesh). Characterizations and Measurements. 1 H NMR spectra were obtained at Bruker ARX400 spectrometer using tetramethylsilane (TMS) as the internal standard. EI mass spectrometric measurements were obtained on the SHIMADZU GCMS-QP2010 pulse spectrometer. Single crystal X-ray diffraction data were collected on a Rigaku Saturn X-ray diffractometer with graphite-monochromator Mo-Kα radiation (λ = Å) at 173 K. Intensities were collected for absorption effects using the multi-scan technique SADABS. The structures were solved by direction methods and refined by a full matrix least squares technique based on F2 using SHELXL 97 program (Sheldrick, 1997). The extended packing plots and data from crystal packing were obtained using the software Mercury SEM images were taken from Hitachi S-4800 microscopes at an accelerating voltage of 15 kv. TEM images were taken from a JEOL JEM-1011 microscope at an accelerating voltage of 100 kv. The aggregate nanostructures of the DBD and BBD were prepared in silicon slide for SEM and copper grids for TEM. UV-Vis spectra were measured on a Hitachi U-3010 spectrometer. The fluorescence spectra were measured on a Hitachi F-4500 spectrometer. Fluorescence images of the microstructures were taken by using a laser-based fluorescence microscope (Olympus IX81) and an intensified charge-coupled device (CCD, Olympus DP71) detection system. The NLO measurements were studied using a laser scanning microscope with the pump at 800 S-2
3 nm (Spectra Physics Mai-Tai, pulse width: 100 fs, repetition rate: 82 MHz) in a reflection geometry with incident and detection angles both at 45.The NLO signal was led through a fiber waveguide to a monochromator (Princeton Instruments), and sent to be detected by a charge-coupled device (CCD) or photomultiplier tube (PMT). The polarization state of the incident beam was controlled with a half-wave-plate. Table S1. Crystal data and structure refinement for DBD and BBD. Identification code mx2989 mx3432 Empirical formula C 24 H 12 N 2 O 2 C 26 H 16 N 2 O 4 Formula weight Temperature K K Wavelength Å Å Crystal system, space group Monoclinic, P 1 21/c 1 Monoclinic, C 1 2/c 1 Unit cell dimensions a = (3) Å α= 90. b = (14) Å β= (3). c = (4) Å γ = 90. a = (7) Å α= 90. b = 9.176(3) Å β= (4). c = 9.967(3) Å γ = 90. Volume (7) Å (10) Å 3 Z, Calculated density 4, Mg/m Mg/m 3 Absorption coefficient mm mm -1 F(000) Crystal size 0.35 x 0.31 x 0.07 mm x 0.12 x 0.05 mm 3 Theta range for data collection to to Index ranges -19<=h<=15, -8<=k<=8, -19<=l<=23-30<=h<=30, -11<=k<=11, -12<=l<=12 Reflections collected / unique 12342/4120 [R(int) = ] 7011/2312 [R(int) = ] S-3
4 Completeness to theta = % 99.2 % Absorption correction Semi-empirical from equivalents Semi-empirical from equivalents Max. and min. transmission and and Refinement method Full-matrix least-squares on F 2 Full-matrix least-squares on F 2 Data / restraints / parameters 4120 / 0 / / 0 / 146 Goodness-of-fit on F^ Final R indices [I>2sigma(I)] R1 = , wr2 = R1 = , wr2 = R indices (all data) R1 = , wr2 = R1 = , wr2 = Largest diff. peak and hole and e.å and e.å -3 S-4
5 Figure S1. 1 H NMR spectrum of DBD. S-5
6 Figure S2. 13 C NMR spectrum of DBD. Figure S3. 1 H NMR spectrum of BBD. S-6
7 Figure S4. TOF MS spectrum and elemental analysis report of BBD. S-7
8 Figure S5. TOF MS spectrum and elemental analysis report of DBD. S-8
9 DFT Computations For compounds DBD and BBD, DFT calculations were performed using the Gaussian 09 program. Geometries were optimized in the gas phase using the ωb97xd functional and 6-311g* basis set on all atoms. The geometrical structure and Cartesian coordinates of the compounds DBD and BBD at the ground and excited states are shown in Table S2 and S3, respectively. Table S2. The geometrical structure and Cartesian coordinates of the compound DBD and BBD at the ground states. BBD DBD Row Symbol X Y Z Row Symbol X Y Z 1 C C C C C C C C C C C C C O C O H C O H S-9
10 11 C C H H C C O C C C C C C H C C H H C C H H C H H H H C C C C C C C C C H H C C H H C C H H H H C H S-10
11 36 N C C C N C C N H N H H C H H H O O Table S3. The geometrical structure and Cartesian coordinates of the compound DBD and BBD at the excited states. BBD DBD Row Symbol X Y Z Row Symbol X Y Z 1 C C C C S-11
12 3 C C C C C C C C C O C O H C O H C C H H C C O C C C C C C H C C H H C C H H C H H H H C C C C C C C S-12
13 28 C C H H C C H H C C H H H H C H N C C C N C C N H N H H C H H H O O S-13
14 Figure S6. Simulated absorbance spectra of BBD and DBD. S-14
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