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Materials 2021, 14, 1786 4 of 20 Table 1. Selected crystal and structure refinement data for the CPs: SmCP1, TbCP1, TbCP2 and TbCP3. Formula Mr Crystal morphology Crystal size/mm Crystal system Space group a/Å b/Å c/Å β/ ◦ Volume/Å3 SmCP1 C16H29N2O17Sm 671.76 Colorless plates/prisms 0.18 × 0.07 × 0.05 Monoclinic P21/n 7.1362(2) 22.6821(6) 14.2428(4) 92.0350(10) 2303.94(11) TbCP1 C16H29N2O17Tb 680.33 Colorless needles 0.19 × 0.05 × 0.04 Monoclinic P21/n 7.1046(8) 22.583(2) 14.2477(16) 92.039(6) 2284.5(4) TbCP2 C16H17N2O11Tb 572.23 Pink prisms 0.33 × 0.10 × 0.08 Monoclinic P21/c 11.8098(8) 10.7888(7) 14.3259(8) 100.253(2) 1796.2(2) TbCP3 C28H21N4O9Tb 716.41 Colorless plates 0.19 × 0.06 × 0.04 Monoclinic P21/c 10.350(2) 21.289(5) 12.490(3) 104.125(9) 2668.9(10) Z4444 ρcalculated /gcm-3 Final R índices [I > 2σ (I)] R índices (all data) 1.937 R1 = 0.0275 wR2 = 0.0568 R1 = 0.0363 wR2 = 0.0611 1.978 R1 = 0.0494 wR2 = 0.0863 R1 = 0.0958 wR2 = 0.1024 2.116 R1 = 0.0324 wR2 = 0.0611 R1 = 0.0400 wR2 = 0.0634 2.714 R1 = 0.0476 wR2 = 0.0818 R1 = 0.0906 wR2 = 0.0960 2.4. Materials Characterization Powder X-ray diffraction (PXRD) patterns were collected at room temperature using a Rigaku SmartLab diffractometer (Cu Kα1,2 radiation, λ1 = 1.540593 Å and λ2 = 1.544414 Å) equipped with a D/teX Ultra 250 silicon strip detector and zero-background sample holder in a Bragg-Brentano para-focusing optics configuration (45 kV, 200 mA). Intensity data were obtained by the step counting method (step: 0.01◦) in continuous mode in the approximate range 3.0◦ ≤ 2θ ≤ 50◦. Fourier transform infrared (FT-IR) spectra were obtained neatly with a FT-IR Perkin Elmer Spectrum BX with an attenuated total reflectance (ATR) accessory in the 400–4000 cm−1 range. Scanning electron microscope (SEM) images and electron dispersive X-ray spec- troscopy (EDX) spectra were acquired at CEMUP (Center of Materials from University of Porto) using a FEI Quanta 400FEG ESEM/EDAX Genesis X4M (15 keV). 2.5. Photoluminescence Characterization The samples were prepared using two different methods, powder and PMMA en- capsulation. In the powder method, crystalline material of the CPs was used to fill the aluminum sample holder with 2 mm diameter hole, and glass cover slides placed to cover the CP. The cover slides and aluminum sample holder were fixed with Teflon. In the PMMA encapsulation, 1–2 mg of the CP was placed on cleaned quartz substrate. One drop of 10 mg/mL PMMA in toluene was dropped on the CP powder to immobilize the powder to the substrate while acquiring the photoluminescence (PL) spectra. The prepared films of CP were then dried in air. PL and PL excitation spectra were recorded at room temperature in a spectrofluorime- ter FluoroMax-4 Horiba Jobin Yvon). PL was detected under 90◦ and long-pass filters were employed to minimize stray light caused by scattering of the excitation light by the powder. Time-resolved PL measurements were performed with a passive Q-switch Nd:YAG laser (TEEM Photonics) as an excitation source, delivering pulses at 355 nm of 300 ps duration at 75 Hz repetition rate. The PL was wavelength-dispersed and filtered by an Acton Research SP2500 spectrometer (f = 500 mm) and subsequently detected with a PicoQuant PMA 06 thermoelectrically cooled hybrid photomultiplier connected to a Picoquant TimeHarp 260 time-correlated single photon counting and multichannel scaling board electronics with 1 ns resolution. The decay time fitting analysis was carried out using Fluofit software (professional version) from PicoQuant.PDF Image | Green Chemistry with Supercritical CO2 and Enzymes
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