Electronic Supporting Information. Photophysical properties of 3-[2-(Nphenylcarbazolyl)benzoxazol-5-yl]alanine
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1 Electronic Supporting Information Photophysical properties of 3-[2-(Nphenylcarbazolyl)benzoxazol-5-yl]alanine derivatives experimental and theoretical studies Katarzyna Guzow a, *, Marlena Czerwińska a, Agnieszka Ceszlak a, Marta Kozarzewska a, Mariusz Szabelski b,c, Cezary Czaplewski a, Anna Łukaszewicz b, Aleksander A. Kubicki b, Wiesław Wiczk a a Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, Gdańsk, Poland b Institute of Experimental Physics, Faculty of Mathematics, Physics and Informatics, Univeristy of Gdańsk, Wita Stwosza 57, Gdańsk, Poland c Current address (M. Sz.): Department of Physics and Biophysics, University of Warmia and Mazury in Olsztyn, Oczapowskiego 4, Olsztyn, Poland * corresponding author: kasiag@chem.univ.gda.pl 1
2 Figure 1S. Fluorescence spectra of 2 in dimethoxyethane and DMF as well as the spectrum of its exciplex formed in dimethoxyethane obtained as a difference between these spectra. Figure 2S. Fluorescence intensity decay observed at 380 nm and 490 nm as well as timeresolved spectra of 2 in dimethoxyethane. 2
3 Table 1S. The values of estimated coefficients (y 0 and a) and their standard errors as well as regression coefficients (r) obtained from the linear fit of photophysical properties (νɶ abs, νɶ fluo, νɶ, φ F and τ) of 1 versus E N T solvent polarity scale. Np denotes a number of solvents used in the analysis. Compound 1 y Equation y=(y 0 ±a) + (b±c)*e T N y 0 ±a b±c r Np νɶ abs [cm -1 ] νɶ fluo [cm -1 ] νɶ [cm -1 ] φ F τ [ns] all solvents 29350±40 -(230±90) aprotic 29370±50 -(260±200) protic 29390±180 -(170±290) all solvents 26140±390 -(5900±840) aprotic 26930±350 -(10920±1290) protic 27560±1050 -(7550±1680) all solvents 3210± ± aprotic 2450± ± protic 1830± ± all solvents 0.65±0.06 -(0.12±0.12) aprotic 0.70±0.05 -(0.57±0.20) protic 1.18±0.14 -(0.90±0.22) all solvents 1.83± ± aprotic 1.21± ± protic 0.87± ±
4 Table 2S. The values of estimated coefficients (y 0 and a) and their standard errors as well as regression coefficients (r) obtained from the linear fit of photophysical properties (νɶ abs, νɶ fluo, νɶ, φ F and τ) of 2 versus E N T solvent polarity scale. Np denotes a number of solvents used in the analysis. Compound 2 y Equation y=(y 0 ±a) + (b±c)*e T N y 0 ±a b±c r Np νɶ abs [cm -1 ] νɶ fluo [cm -1 ] νɶ [cm -1 ] φ F all solvents 30711±94 -(769±220) aprotic 30643±50 -(274±171) protic 30480±1050 -(558±1660) all solvents 26688±64 -(1682±149) aprotic 26736±57 -(2119±195) protic 27686±319 -(3094±505) all solvents a 4023± ± aprotic 3907± ± protic 2794± ± all solvents a 0.74± ± aprotic 0.72± ± protic 0.93± ± τ [ns] all solvents b 2.01±0.08 -(0.65±0.18) aprotic 2.11±0.10 -(1.17±0.39) protic 1.02± ± a without formamide b without formamide and dimethoxyethane 4
5 Table 3S. Estimated from eq. 3 coefficients (y o. a SPP, b SA, c SB ), their standard errors and correlation coefficients (r) for the multiple linear regression analysis of νɶ abs, νɶ fluo, νɶ, φ F, τ of 1 as a function of Catalán three-parameter solvent scale. y y 0 SPP SA SB r νɶ abs [cm -1 ] 29438± ±41 -(276±87) -(263±72) -(2±62) -(26±101) νɶ fluo [cm -1 ] 27340±371 -(4857±651) -(1359±460) -(1005±755) νɶ [cm -1 ] -(3909±860) -(3782±836) φ F 0.82± ± ± ±1080 -(0.54±0.20) -(0.55±0.19) 2148± ±584 -(0.02±0.10) 0.35± ±0.09 -(447±567) τ [ns] -(4.04±0.51) 9.77± ±0.36 -(0.66±0.34) Table 4S. Estimated from eq. 2 coefficients (y o, a π*, b α, c β,), their standard errors and correlation coefficients (r) for the multiple linear regression analysis of νɶ abs, νɶ fluo, νɶ, φ F, τ of 1 as a function of Kamlet-Taft solvent scale. y y 0 π * α β r νɶ abs [cm -1 ] 29438± ±41 -(276±87) -(263±72) -(2±62) -(26±101) νɶ fluo [cm -1 ] 27340±371 -(4857±651) -(1359±460) -(1005±755) νɶ [cm -1 ] 2098± ±370 φ F 0.53± ±0.05 τ [ns] 1.00± ± ± ±643 -(0.25±0.10) -(0.24±0.09) 3.87± ± ± ±396 -(0.02±0.07) 0.27± ± ± ± ± ±
6 Table 5S. Estimated from eq. 3 coefficients (y o. a SPP, b SA, c SB ), their standard errors and correlation coefficients (r) for the multiple linear regression analysis of νɶ abs, νɶ fluo, νɶ, φ F, τ of 2 as a function of Catalán three-parameter solvent scale. y y 0 SPP SA SB r νɶ abs [cm -1 ] 31027± ±269 νɶ fluo [cm -1 ] 27354± ±255 νɶ [cm -1 ] 3679± ±322 φ F 0.40± ±0.12 -(678±426) -(516±363) -(1361±399) -(1238±343) 672± ± ± ±0.15 -(1002±252) -(958±235) -(1606±326) -(1536±222) 596± ±281 -(154±200) (142±188) ± ±0.12 -(0.01±0.09) τ [ns] 2.86±0.25 -(1.25±0.37) 1.38±0.22 -(2.29±0.18) Table 6S. Estimated from eq. 2 coefficients (y o, a π*, b α, c β,), their standard errors and correlation coefficients (r) for the multiple linear regression analysis of νɶ abs, νɶ fluo, νɶ, φ F, τ of 2 as a function of Kamlet-Taft solvent scale. y y 0 π * α β r νɶ abs [cm -1 ] 30721± ±85 νɶ fluo [cm -1 ] 26760± ±78 νɶ [cm -1 ] 3962± ±96 φ F 0.73± ±0.04 τ [ns] 2.16± ±0.08 -(458±165) -(393±154) -(974±152) -(928±140) 515± ± ± ±0.06 -(0.44±0.14) -(0.44±0.14) -(579±159) -(467±119) -(780±147) -(699±109) 216± ± ± ±0.05 -(229±216) (164±199) ± ± (0.08±0.14) -(0.26±0.19) -(0.34±0.14)
7 Table 7S. Theoretically calculated absorption wavelengths (for f 0.1) for 1 using def2- TZVP/pbe0 functional. acetonitrile cyclohexane λ [nm] f MO contribution (%) λ [nm] f MO contribution (%) HOMO LUMO HOMO LUMO HOMO LUMO HOMO LUMO HOMO-2 LUMO HOMO-2 LUMO HOMO-3 LUMO HOMO-2 LUMO HOMO-1 LUMO+1 HOMO LUMO HOMO LUMO+4 HOMO-4 LUMO HOMO-1 LUMO+1 HOMO-2 LUMO+2 HOMO-1 LUMO+6 HOMO LUMO+7 HOMO-1 LUMO+3 HOMO-4 LUMO+1 HOMO-1 LUMO+3 HOMO-1 LUMO HOMO-1 LUMO+6 HOMO LUMO+4 HOMO-2 LUMO+2 HOMO-6 LUMO HOMO-2 LUMO+3 HOMO-1 LUMO+4 HOMO LUMO+3 HOMO-3 LUMO+1 HOMO LUMO+5 HOMO-2 LUMO+1 HOMO-6 LUMO HOMO-3 LUMO HOMO-4 LUMO HOMO LUMO+4 HOMO-4 LUMO HOMO-1 LUMO+1 HOMO-1 LUMO+6 HOMO LUMO+7 HOMO-2 LUMO+2 HOMO-1 LUMO+3 HOMO-4 LUMO+1 HOMO-1 LUMO+3 HOMO-1 LUMO HOMO LUMO+4 HOMO-1 LUMO+6 HOMO-5 LUMO HOMO-6 LUMO HOMO-2 LUMO+3 HOMO-1 LUMO+4 HOMO LUMO
![Table 8S. Theoretically calculated absorption wavelengths (for f 0.1) for 2 using def2- TZVP/pbe0 functional. acetonitrile cyclohexane λ [nm] f MO contribution (%) λ [nm] f MO contribution (%) 326.](/docs-images/92/109513912/images/8-0.jpg "2 0.580 HOMO LUMO HOMO LUMO+1 85.4 8.2 323.5 0.490 HOMO LUMO HOMO LUMO+1 78.6 13.7 315.9 0.210 HOMO LUMO+1 HOMO-1 LUMO HOMO LUMO 71.5 14.8 8.5 314.3 0.350 HOMO+1 LUMO+1 HOMO LUMO HOMO-1 LUMO 67.5 15.")
8 Table 8S. Theoretically calculated absorption wavelengths (for f 0.1) for 2 using def2- TZVP/pbe0 functional. acetonitrile cyclohexane λ [nm] f MO contribution (%) λ [nm] f MO contribution (%) HOMO LUMO HOMO LUMO HOMO LUMO HOMO LUMO HOMO LUMO+1 HOMO-1 LUMO HOMO LUMO HOMO+1 LUMO+1 HOMO LUMO HOMO-1 LUMO HOMO-2 LUMO HOMO-2 LUMO+1 HOMO LUMO+1 HOMO-1 LUMO+2 HOMO-3 LUMO+6 HOMO LUMO+7 HOMO-2 LUMO+3 HOMO LUMO+1 HOMO-1 LUMO+3 HOMO LUMO HOMO-1 LUMO HOMO-1 LUMO HOMO-1 LUMO+1 HOMO LUMO+1 HOMO LUMO HOMO-1 LUMO+1 HOMO-3 LUMO HOMO-2 LUMO HOMO LUMO+5 HOMO LUMO+2 HOMO-1 LUMO HOMO LUMO Figure 3S. HOMO and LUMO orbitals of 1. 8
9 Figure 4S. HOMO and LUMO orbitals of 2. Figure 5S. Theoretically calculated structure of 1 in the ground (green) and excited state (yellow) with the orientation of the dipole moments in the ground (red arrow) and excited state (blue arrow) as well as transition dipole moment in emission (green arrow). The excited state dipole moment and transition dipole moment are enlarged for 3 and 200 times, respectively. The transition dipole moment in absorption is not presented because of overlapping with the transition dipole moment in emission. 9
10 Figure 6S. Theoretically calculated structure of 2 in the ground (green) and excited state (yellow) with the orientation of the dipole moments in the ground (red arrow) and excited state (blue arrow) as well as transition dipole moment in emission (green arrow). The transition dipole moment in absorption is not presented because of too small angle (4.1 degree) between both transition dipole moments. 10
11 The experimentally obtained emission anisotropy course can be fitted with the expression obtained by Kawski and Gryczyński: r ( β, Rd ) = r ( Rd ) cos β 2 2 ( ) r R d where: ( a 1) + 2a ( a 1) 3a arcsin 3 a 1 = ( a 1) 2arcsin a a 2 = R 2 d 2 ( Rd 1) R d denotes the stretching factor and β denotes the angle between the transition dipole moment in absorption and emission. Figure 7S. Emission anisotropy versus linear dichroism R d for 1 in PVA film at 293 K. Solid line has been obtained from Kawski-Gryczyński model and the best fit to experimental data was obtained for the value of β specified in the text box. 11
12 Figure 8S. Emission anisotropy versus linear dichroism R d for 2 in PVA film at 293 K. Solid line has been obtained from Kawski-Gryczynski model and the best fit to experimental data was obtained for the value of β specified in the text box. 12
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