Supporting Information. for. Systematic Molecular Engineering of a Series of Aniline-based Squaraine Dyes and Their. Structure-related Properties
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1 Supporting Information for Systematic Molecular Engineering of a Series of Aniline-based Squaraine Dyes and Their Structure-related Properties Taihong Liu, a,b Xinglei Liu, a Weina Wang, b Zhipu Luo, c Muqiong Liu, d Shengli Zou, d Cristina Sissa, e Anna Painelli, e Yuanwei Zhang, a Mikas Vengris, f Mykhailo V. Bondar, g David J. Hagan, h Eric W. Van Stryland, h Yu Fang, b and Kevin D. Belfield *a,b a Department of Chemistry and Environmental Science, College of Science and Liberal Arts, 323 Martin Luther King, Jr. Blvd., New Jersey Institute of Technology, Newark, NJ 07102, United States b School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi an, , P. R. China c Synchrotron Radiation Research Section, National Cancer Institute, Argonne National Laboratory, Argonne, IL 60439, United States d Department of Chemistry, University of Central Florida, Orlando, FL 32816, United States e Department of Chemistry, Life Science and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, Parma, 43124, Italy f Light Conversion, Keramiku 2B, LT10233, Vilnius, Lithuania g Institute of Physics National Academy of Science of Ukraine, Prospect Nauki, 46, Kiev-28, 03028, Ukraine h The College of Optics and Photonics (CREOL), University of Central Florida, P.O. Box , Orlando, FL, United States * Belfield@njit.edu Table of contents 1. Experimental details... S2 2. Different synthesis strategy for SD-4... S3 3. Overlay of the 13 C NMR spectra of the dyes... S5 4. Results of quantum chemical calculations... S6 5. Essential state models (additional information)... S H and 13 C NMR spectra of the compounds... S11 S1
2 7. LR- and HR-MS of the compounds... S16 8. Crystallography... S21 9. References... S28 1. Experimental Details 1.1. Materials and Methods. All reagent chemicals and solvents were used as purchased without further purification unless otherwise noted. Thin-layer chromatography (TLC) was performed on pre-coated silica gel 60 F254 plates. Column chromatography was performed over silica gel mesh. The 1 H and 13 C NMR measurements were performed at room temperature by a Bruker Avance III NMR spectrometer at 500 and 126 MHz, respectively. Highresolution mass spectrometry (HR-MS) analysis was performed on an Apex Ultra 70 Hybrid. HR-MS (Bruker Daltonics) using ESI techniques were obtained at the Department of Chemistry, Rutgers University-Newark, Newark, NJ. Low-resolution LC-MS analysis was performed using a Thermo Scientific Ultimate 3000 in ESI mode. The molecular geometries of the investigated dyes, the highest occupied molecular orbital (HOMO), and the lowest unoccupied molecular orbital (LUMO) states were calculated in the framework of the density functional theory (DFT) at the B3LYP/6-31G(d) level in a suite of Gaussian 03 programs Photophysical and Photochemical Measurements. The optical properties of the dyes were investigated at room temperature in spectroscopic-grade solvents: toluene (TOL), tetrahydrofuran (THF), dichloromethane (DCM), acetonitrile (ACN), methanol (MeOH), and dimethyl sulfoxide (DMSO). UV-vis spectra were recorded using a Tecan Infinite M200 PRO spectrometer in 10 mm path length quartz cuvettes. The steady-state fluorescence emission spectra were recorded with an Edinburgh Instruments FLS980 fluorescence spectrometer. Fluorescence lifetimes (τ F ) were determined with the single photon counting technique (TCSPC) and the same fluorescence spectrometer using a pulsed picosecond diode laser (EPL-635) as the excitation source. It should be mentioned that under the employed experimental conditions, the S2
3 maximum optical density of the investigated solutions did not exceed 0.1 and all reabsorption effects were negligible. The measurements of fluorescence quantum yield (Φ F ) were performed using the standard procedure with cresyl violet (Φ F =0.54 in MeOH) as a reference. 1 The fundamental excitation anisotropy spectrum of the dyes, r 0, was obtained in viscous polytetrahydrofuran (pthf) at room temperature. In this case, the observed experimental value of anisotropy r=r 0 /(1+ τ F /θ) is close to the r 0, where depolarization effects related to molecular rotational motion are negligible (i.e., the molecular rotational correlation time, θ τ F ). The photochemical stability was investigated quantitatively by measuring the photochemical decomposition quantum yield, Φ ph =N ph /N hv (N ph and N hv are the numbers of decomposed molecules and absorbed photons, respectively). The values of Φ ph were determined by an absorption method using a continuous wave (CW) diode laser for excitation of the dyes into the main absorption band (excitation wavelength 650 nm, average beam irradiance 80 mw/cm 2 ). 2-4 A lens was used to expand the beam to irradiate the entire volume of the sample in a 1 mm path length quartz cuvette. According to the well-developed absorption methodology, the values of Φ ph can be determined by the following equation 5,6 : Φ ph = (A t A 0 )N A 10 3 ε I [110 (At+A 0 )/2 ] t A t and A 0 are absorbance maximum at time points t and t 0, respectively. N A is Avogadro s number, ε is the molar extinction coefficient (M -1 cm -1 ), I is the intensity of laser (photon cm -2 s - 1 ), and t is the irradiation time (s). The stock solutions were made at a concentration of ~1.0 mm by dissolving squaraine dyes into THF. For the aggregation studies, a series of blank solvent blends were prepared with varying DMSO/H 2 O ratios. The final solution was made by injecting a corresponding volume of stock solution into the cuvette with 3 ml blank solvent blends. 2. Different Synthesis Strategy for SD-4 S3
4 One main method including two steps has been tried for the synthesis of dye SD-4. Firstly, compound 2 was synthesized by reacting intermediate 1 with excess dimethyl sulfate in the presence of potassium tert-butoxide in THF. The crude product was purified by column chromatography using n-hexane/ethyl acetate (20/1, v/v) as the eluent to afford 2 as yellowish oil. 1 H NMR (400 MHz, CDCl 3, ppm): δ 5.85 (s, 2 H), 5.82 (s, 1 H), 3.76 (s, 6 H), (4 H), (2 H), (16 H), (12 H). 13 C NMR (100 MHz, CDCl 3, ppm): δ , , 91.89, 87.49, 56.58, 55.03, 36.96, 30.78, 28.71, 23.99, 23.25, 14.09, Unfortunately, the condensation between 2 and squaric acid didn t give any designed product. Scheme S1. Different synthetic route for SD-4 S4
5 3. Overlay of the 13 C NMR Spectra of the Dyes Figure S1. Overlay of the 13 C NMR spectra of the dyes. (Note: individual 13 C NMR spectrum for each dye is attached below) S5
6 4. Results of Quantum Chemical Calculations SD-0 SD-1 SD-2a SD-2b SD-3 SD-4 Figure S2. The DFT-calculated molecular structures of the dyes at B3LYP/6-31G(d) level. S6
7 Side View Top view LUMO SD-0 HOMO LUMO SD-1 HOMO LUMO SD-2b HOMO S7
8 Side View Top view LUMO SD-3 HOMO LUMO SD-4 HOMO Figure S3. Molecular orbital contours of the HOMO and LUMO for the dyes at B3LYP/6-31G(d) level. S8
9 5. Essential State Models (Additional Information) The Hamiltonian in Eq. 4 describes a squaraine molecule experiencing a reaction field F whose relevant components are along the main molecular axis x and y (see Fig. 8). Since the two components of the reaction field, F x and F y, can be treated as classical variables, we diagonalize the molecular problem on a grid of F x and F y values. For each (F x, F y ) value, we write the Hamiltonian matrix on the non-adiabatic basis obtained as the direct product of the 4 electronic basis states defined in Fig. 8, times the eigenstates of the two harmonic oscillators associated with the two vibrational coordinates (Q 1 and Q 2 in Eq. 3). The harmonic oscillator basis has infinite dimension, and we truncate the basis to account for states containing up to 6 vibrational quanta (we checked for convergence). The resulting (F x, F y )-dependent eigenstates are the vibronic states as relevant to spectroscopy. Specifically, corresponding transition frequencies and dipole moments enter into the sum over states expressions for optical spectra (explicit expressions are given below) to calculate (F x, F y )-dependent optical spectra. The overall solution spectra are finally obtained summing up spectra calculated for different (F x, F y ) values, weighting each spectrum according to the Boltzmann distribution of the relevant state. Specifically, for linear and 2-photon absorption spectra we consider the Boltzmann distribution relevant to the (F x, F y )-dependent ground-state energy, while for fluorescence spectra we consider the Boltzmann distribution relevant to the (F x, F y )-dependent energy of the fluorescent state. The sum over state expression for the linear absorption coefficient (M -1 cm -1 units) is: 2 N ~ ~ ~ ~ 10π Aν ν gn ν ε ( ν ) = gn exp 3ln10! cε 0 σ 2π n 2 σ where ν is the wavenumber (cm -1 units), N A the Avogadro number, c the light velocity, ε 0 the vacuum dielectric constant; σ is the width of the Gaussian bandshape assigned to each vibronic transition, related to the intrinsic linewidth as σ = 2γ/ Moreover, μ!" and ν!" are the S9
10 S10 transition dipole moment and energy from the ground state (g) to the excited state (n) and the sum runs over all excited states. The fluorescence spectrum is calculated as: n fn fn I ~ ~ 2 1 exp 2 ~ ) ~ ( σ ν ν π σ ν ν where f is the fluorescent state and the sum runs over all states with energy lower than the fluorescent state. The two-photon absorption cross section is calculated as (cgs units): ( ) γ π σ =,, ; Im 4 ) ( n c! where ( ) ( )( )( ) ( )( )( ) ( )( )( ) ( )( )( ) Ω Ω Ω + Ω Ω Ω + Ω Ω Ω + Ω Ω Ω = γ ng mg lg l k i j ng mg lg k l j i ng mg lg l k i j ng mg lg l k j i lmn ijkl g n n m m l l g g n n m m l l g g n n m m l l g g n n m m l l g ,, ; * * 3!
11 6. 1 H and 13 C NMR Spectra of the Compounds Figure S4. 1 H NMR spectrum of SD-0. Figure S5. 13 C NMR spectrum of SD-0. S11
12 Figure S6. 1 H NMR spectrum of SD-1 (Similar signals based on the intramolecular noncovalent interactions in asymmetrical squaraines were also reported in Ref. 7, and explained by the presence of conformational isomers with the support from variable temperature NMR results). Figure S7. 13 C NMR spectrum of SD-1 (c. f. Ref. 7). S12
13 Figure S8. 1 H NMR spectrum of SD-2a. Figure S9. 13 C NMR spectrum of SD-2a. S13
14 Figure S10. 1 H NMR spectrum of SD-2b. Figure S C NMR spectrum of SD-2b. S14
15 Figure S12. 1 H NMR spectrum of SD-3. Figure S C NMR spectrum of SD-3. S15
16 7. LR- and HR-MS of the Compounds Figure S14. HR-MS (upper) and LR-MS (lower) of SD-0. S16
17 Figure S15. HR-MS (upper) and LR-MS (lower) of SD-1. S17
18 Figure S16. HR-MS (upper) and LR-MS (lower) of SD-2a. S18
19 Figure S17. HR-MS (upper) and LR-MS (lower) of SD-2b. S19
20 Figure S18. HR-MS (upper) and LR-MS (lower) of SD-3. S20
21 8. Crystallographic Summary of Dye SD-2a Table S1. Crystal data and structure refinement for SD-2a Empirical formula C 50 H 80 N 2 O 6 Formula weight Temperature/K 100(2) Crystal system triclinic Space group P-1 a/å (6) b/å (10) c/å (11) α/ (14) β/ (16) γ/ (14) Volume/Å (3) Z 2 ρ calc g/cm /mm F(000) Crystal size/mm Radiation synchrotron (λ = ) 2Θ range for data collection/ to Index ranges -11 h 11, -19 k 19, -22 l 22 Reflections collected Independent reflections 9919 [R int = , R sigma = ] Data/restraints/parameters 9919/391/741 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = S21
22 Table S2. Fractional atomic coordinates ( 10 4 ) and equivalent isotropic displacement parameters (Å ) for SD-2a. U eq is defined as 1/3 of the trace of the orthogonalised U IJ tensor. Atom x y z U(eq) O1 7540(2) (15) (13) 65.9(6) O2 7057(2) (15) (12) 63.1(6) O (2) (17) (17) 80.6(8) N1 8788(4) 7186(2) (19) 87.5(10) C1 9767(3) (16) 434.8(16) 50.0(6) C2 8888(3) (18) (16) 53.3(7) C (2) (14) (13) 74.1(9) C4 9031(2) (14) (12) 70.7(9) C (18) (14) (12) 63.5(8) C (16) (12) (11) 55.4(7) C (19) (11) 1055(1) 54.4(7) C (16) (13) (12) 65.2(8) C9 5563(4) 9316(3) 1292(2) 72.8(9) C (7) 6645(3) 2992(3) 109.5(17) C (6) 7174(3) 3121(3) 102.1(15) C (7) 5857(3) 2509(3) 123(2) C (9) 5194(4) 2515(4) 131(2) C (7) 5499(4) 2777(4) 132(2) C (9) 7956(6) 4306(4) 157(3) C (10) 5997(6) 2574(5) 158(3) C (8) 7983(5) 3661(4) 132(2) C (11) 8115(8) 3838(6) 184(4) C (13) 4404(5) 1967(6) 180(4) C (19) 6028(11) 1776(8) 248(6) C (20) 5213(10) 1519(10) 269(7) C (13) 7494(9) 4323(8) 217(5) C (17) 7590(13) 4488(12) 275(7) C (14) 8831(8) 4846(6) 207(5) C (30) 6700(20) 4610(20) 443(18) O4 2966(3) (17) (15) 81.5(8) C (4) (19) (16) 60.2(8) C (4) 4902(2) (17) 62.9(8) O5 1761(9) 4074(8) 4280(5) 79(3) O6 6680(7) 3876(5) 3391(4) 71.6(15) N2 2867(8) 2126(5) 2131(4) 77.5(19) C (6) 3032(4) 2796(3) 64.3(16) C (6) 3644(4) 3371(4) 58.8(19) S22
23 C (7) 3978(5) 3870(3) 58(2) C (6) 3701(5) 3796(4) 51.6(18) C (5) 3090(4) 3221(4) 65(2) C (6) 2756(4) 2722(3) 66.9(19) C (11) 1769(6) 2106(5) 85(2) C35 217(9) 3804(8) 4249(8) 94(3) C (12) 1037(7) 2654(7) 95(3) C (15) -389(7) 3209(7) 116(3) C (14) 263(6) 2560(7) 102(3) C39-543(13) 770(10) 2608(8) 116(4) C (18) 821(17) 3148(13) 180(9) C (20) 1152(16) 3811(13) 213(9) C (12) 1230(10) 3165(8) 143(4) C (10) 1792(5) 1604(3) 77.2(18) C (8) 1992(6) 552(4) 89(2) C (9) 2397(5) 983(4) 85(2) C (12) 1960(9) 971(6) 132(4) C (11) 2565(6) 458(5) 106(3) C (15) 3210(9) -142(7) 143(4) C (14) 3537(9) -525(7) 132(4) C50 870(30) 4096(16) -73(13) 212(8) O7 1458(12) 4102(7) 4528(5) 65(2) O8 5999(12) 3981(7) 3258(4) 76(2) N3 2001(15) 2261(5) 2264(4) 81(3) C (10) 3178(5) 2793(3) 69(2) C (8) 3748(5) 3365(4) 59(2) C (9) 4019(5) 3961(3) 60(4) C (9) 3719(5) 3984(4) 47(2) C (9) 3149(5) 3412(4) 66(3) C (10) 2878(4) 2816(3) 69(3) C57 519(16) 1833(7) 2311(5) 89(3) C58-78(11) 3846(8) 4589(6) 69(2) C59 546(19) 1090(10) 2859(9) 112(5) C (50) -80(30) 3460(20) 280(20) C (30) 313(17) 2704(17) 172(11) C62-955(18) 651(10) 2850(10) 111(5) C (30) 560(14) 3285(11) 137(6) C (20) 1150(30) 2349(17) 360(30) C (20) 1280(16) 2752(16) 190(9) C (18) 1951(6) 1617(5) 92(4) S23
24 C (13) 2216(9) 419(6) 96(3) C (12) 2567(6) 982(5) 89(3) C (20) 2550(20) 728(14) 186(9) C (13) 2738(7) 601(5) 97(3) C (20) 3419(8) 18(6) 123(5) C (20) 2185(16) 246(13) 169(7) C (19) 2290(18) 566(13) 173(8) S24
25 Table S3. Bond lengths for non-disordered SD-2a. Atom Atom Length/Å Atom Atom Length/Å O1 C (3) C30 C O2 C (2) C31 C O2 C (4) C32 C O3 C (3) C34 C (12) N1 C (3) C36 C (13) N1 C (6) C36 C (12) N1 C (6) C37 C (12) C1 C (4) C39 C (13) C1 C (4) C40 C (15) C1 C (3) C40 C (17) C3 C C43 C (9) C3 C C44 C (10) C4 C C44 C (9) C5 C C45 C (9) C6 C C47 C (11) C7 C C48 C (14) C10 C (7) C49 C (16) C11 C (8) O7 C (9) C12 C (9) O7 C (12) C12 C (8) O8 C (12) C13 C (9) N3 C (9) C14 C (10) N3 C (14) C15 C (9) N3 C (15) C15 C (11) C51 C C16 C (13) C51 C C17 C (11) C52 C C18 C (12) C53 C C20 C (13) C54 C C22 C (14) C55 C C23 C (3) C57 C (15) O4 C (4) C59 C (18) C26 C (5) C59 C (15) C26 C (6) C60 C (19) C26 C (4) C62 C (18) C26 C (5) C63 C (18) O5 C (8) C64 C (18) O5 C (11) C66 C (12) O6 C (7) C67 C (13) S25
26 N2 C (9) C67 C (17) N2 C (9) C68 C (13) N2 C (10) C69 C (17) C28 C C70 C (11) C28 C C72 C (17) C29 C X,2-Y,-Z; 2 1-X,1-Y,1-Z S26
27 Table S4. Bond angles for non-disordered SD-2a. Atom Atom Atom Angle/ Atom Atom Atom Angle/ C6 O2 C (2) C29 C30 C (4) C4 N1 C (3) O5 C31 C (5) C4 N1 C (3) O5 C31 C (5) C11 N1 C (3) C30 C31 C C2 1 C1 C2 88.4(2) C33 C32 C C2 1 C1 C (2) C32 C33 C C2 C1 C (2) C32 C33 N (4) O1 C2 C (3) C28 C33 N (4) O1 C2 C (3) N2 C34 C (7) C1 1 C2 C1 91.6(2) C38 C36 C (8) C4 C3 C C38 C36 C (10) C5 C4 C C34 C36 C (9) C5 C4 N (19) C36 C38 C (10) C3 C4 N (19) C36 C39 C (10) C4 C5 C C42 C40 C (15) O2 C6 C (14) C40 C42 C (11) O2 C6 C (14) N2 C43 C (6) C7 C6 C C46 C44 C (7) C8 C7 C C43 C45 C (7) C8 C7 C (14) C43 C45 C (6) C6 C7 C (14) C47 C45 C (6) O3 C8 C (14) C48 C47 C (8) O3 C8 C (14) C49 C48 C (12) C7 C8 C C48 C49 C (14) N1 C10 C (5) C54 O7 C (9) N1 C11 C (5) C56 N3 C (10) C10 C12 C (5) C56 N3 C (8) C10 C12 C (6) C66 N3 C (8) C13 C12 C (5) C52 C51 C C12 C13 C (6) O8 C52 C (6) C16 C14 C (5) O8 C52 C (6) C17 C15 C (7) C53 C52 C C20 C16 C (11) C52 C53 C C18 C17 C (6) C52 C53 C (4) C18 C17 C (7) C54 C53 C (4) C15 C17 C (6) O7 C54 C (6) C22 C18 C (9) O7 C54 C (6) S27
28 C16 C20 C (13) C55 C54 C C18 C22 C (12) C54 C55 C C25 C23 C (15) C55 C56 C C27 2 C26 C (4) C55 C56 N (7) C27 2 C26 C (3) C51 C56 N (7) C53 C26 C (4) N3 C57 C (11) C27 2 C26 C (4) C61 C59 C (17) C27 C26 C (4) C61 C59 C (16) O4 C27 C (3) C57 C59 C (11) O4 C27 C (3) C59 C61 C60 99(2) C26 2 C27 C (3) C59 C62 C (14) C31 O5 C (8) C65 C64 C (15) C33 N2 C (6) C64 C65 C (15) C33 N2 C (7) N3 C66 C (9) C43 N2 C (7) C68 C67 C (12) C29 C28 C C66 C68 C (9) O6 C29 C (4) C66 C68 C (9) O6 C29 C (4) C67 C68 C (8) C28 C29 C C72 C69 C (17) C31 C30 C C71 C70 C (11) C31 C30 C (4) C69 C72 C (17) 1 2-X,2-Y,-Z; 2 1-X,1-Y,1-Z 9. References (1) Magde, D.; Brannon, J. H.; Cremers, T. L.; Olmsted, J. Absolute Luminescence Yield of Cresyl Violet. A Standard for the Red. J. Phys. Chem. 1979, 83, ; (2) Liu, T.; Bondar, M. V.; Belfield, K. D.; Anderson, D.; Masunov, A. E.; Hagan, D. J.; Stryland, E. W. V. Linear Photophysics and Femtosecond Nonlinear Spectroscopy of a Star- Shaped Squaraine Derivative with Efficient Two-Photon Absorption. J. Phys. Chem. C 2016, 120, (3) Corredor, C. C.; Belfield, K. D.; Bondar, M. V.; Przhonska, O. V.; Yao, S. One- and Two- Photon Photochemical Stability of Linear and Branched Fluorene Derivatives. J. Photochem. Photobiol. A: Chem , 184, ; S28
29 (4) Belfield, K. D.; Mykhailo, V. B.; Liu, Y.; Przhonska, O. V. Photophysical and Photochemical Properties of 5,7-Dimethoxycoumarin Under One- and Two-photon Excitation. J. Phys. Org. Chem. 2003, 16, (5) Sui, B.; Tang, S.; Woodward, A. W.; Kim, B.; Belfield, K. D. A BODIPY-Based Water- Soluble Fluorescent Probe for Mitochondria Targeting. Eur. J. Org. Chem. 2016, 2016, ; (6) Wang, X.; Nguyen, D. M.; Yanez, C. O.; Rodriguez, L.; Ahn, H.-Y.; Bondar, M. V.; Belfield, K. D. High-Fidelity Hydrophilic Probe for Two-Photon Fluorescence Lysosomal Imaging. J. Am. Chem. Soc. 2010, 132, (7) Yang, L.; Zhu, Y.; Jiao, Y.; Yang, D.; Chen Y.; Wu, J.; Lu, Z.; Zhao S.; Pu, X.; Huang, Y. The Influence of Intramolecular Noncovalent Interactions in Unsymmetrical Squaraines on Material Properties, Film Morphology and Photovoltaic Performance. Dyes Pigments 2017, 145, S29
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