difluoroboranyls derived from amides carrying donor group Supporting Information
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1 The influence of the π-conjugated spacer on photophysical properties of difluoroboranyls derived from amides carrying donor group Supporting Information Anna Maria Grabarz a Adèle D. Laurent b, Beata Jędrzejewska c, Anna Zakrzewska c, Denis Jacquemin b,* and Borys Ośmiałowski c,* a Faculty of Chemistry, Wrocław University of Technology, Wyb. Wyspiańskiego 27, PL Wrocław, Poland. b Laboratoire CEISAM, UMR CNRS 6230, Université de Nantes, 2 Rue de la Houssinière, BP92208, Cedex 3 Nantes, France. Denis.Jacquemin@univ-nantes.fr c Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Seminaryjna 3, PL Bydgoszcz, Poland. borys.osmialowski@utp.edu.pl Table of Contents 1. Linear relations for properties of studied compounds S2 2. NMR spectra S3 3. Cartesian coordinates for optimized structures S21 4. Additional fluorescence spectra (fluorescence decomposition, variable temperature spectra) S39 1
2 1. Relationships between Stokes shifts and number of π electrons. Fig. S1. Correlation between the number of conjugated electrons in the space and the Stokes shift (experimental values). We give the correlation equation, together with the determination coefficient (R 2 ) Fig. S2. Correlation between the number of conjugated electrons in the space and the Stokes shift (theoretical values) We give the correlation equation, together with the determination coefficient (R 2 ) 2
3 2. NMR spectra Spectra were recorded on a 400 MHz spectrometer. Spectra of A2 1 H 13 C 3
4 Spectra of A3 1 H 13 C 4
5 Spectra of A4 1 H 13 C 5
6 Spectra of A5 1 H 13 C 6
7 Spectra of A6 1 H 13 C 7
8 Spectra of A7 1 H 13 C 8
9 Spectra of B1 1 H 11 B 9
10 13 C 19 F 10
11 Spectra of B2 1 H 11 B 11
12 13 C 19 F 12
13 Spectra of B3 1 H 11 B 13
14 13 C 19 F 14
15 Spectra of B4 1 H NMR 11 B NMR 13 C NMR 15
16 19 F NMR Spectra of B5 1 H 16
17 11 B 13 C 19 F 17
18 Spectra of B6 1 H 11 B 18
19 13 C 19 F 19
20 Spectra of B7 1 H 11 B 20
21 13 C 19 F 21
22 3. Cartesian coordinates for optimized structures All calculation were performed with M06-2X, GS indicates the ground state structure and ES the excited state structure. 3.1 B1 GS Energy = C N C C C C B F N C N C O F C H H H H H H H H H H ES Energy = C N C C C C B F N C
23 N C O F C H H H H H H H H H H B2(E) GS Energy = C N C C C C B F N C C H O F C H H H H N C C H H H H H H
24 ES H Energy = C N C C C C B F N C C H O F C H H H H N C C H H H H H H H B2(Z) GS Energy = C C N C C C B F N C
25 ES O F C C N C C H H H H H H H H H H H H Energy = C C N C C C B F N C O F C C N C C H H H H H H H H H H
26 H H B3(E) GS Energy = C C N C C C B F N C O F C C C C H H H H H H H N H C C H H H H H H ES Energy = C C N C C
27 C B F N C O F C C C C H H H H H H H N H C C H H H H H H B3(Z) GS Energy = C C C N C C B F N C C C C C N C
28 ES F O C H H H H H H H H H H H H H H Energy = C C C N C C B F N C C C C C N C F O C H H H H H H H H H H
29 H H H H B4 GS Energy = C C C C C C C O B F N C N C C C C C N F C H H H H H H H H H H H H H H ES Energy = C
30 C C C C C C O B F N C N C C C C C N F C H H H H H H H H H H H H H H B5(E) GS Energy = C C N C C C B F N C
31 ES O F C C C H H H H H H C C C C C H H N H H C C H H H H H H Energy = C C N C C C B F N C O F C C C H H
32 H H H H C C C C C H H N H H C C H H H H H H B5(Z) GS Energy = N C C C C C H H H H N C O B C C C C C C C C
33 ES H H N H H H H F F C C H H H H H H Energy = N C C C C C H H H H N C O B C C C C C C C C H H N H H H H
34 F F C C H H H H H H B6(E) GS Energy = C C C N C C B F N C C C C C C F O H H H H H H H H C C C C C H H N H
35 ES H C C H H H H H H Energy = C C C N C C B F N C C C C C C F O H H H H H H H H C C C C C H H N H H C C
36 H H H H H H B6(Z) GS Energy = C C C N C C B F N C C C C C C F O H H H H H H H H C C C C C H H N H H C C H
37 ES H H H H H Energy = C C C N C C B F N C C C C C C F O H H H H H H H H C C C C C H H N H H C C H H H H
38 H H
39 Fluorescence D1 in CHCl 3 EXP 1 2 Fluorescence D2 in CHCl 3 EXP 1 2 Fluorescence D3 in CHCl 3 EXP ν (cm -1 ) ν (cm -1 ) ν (cm -1 ) D4 in CHCl 3 EXP D5 in CHCl 3 EXP D6 in CHCl 3 EXP 1 2 Fluorescence Fluorescence Fluorescence ν (cm -1 ) Fig. S3. Decomposed fluorescence spectra of B1-B6 in CHCl ν (cm -1 ) ν (cm -1 ) 39
40 Absorbance B1 in CHCl 3 Em = 415 nm Em = 384 nm Absorbance B1 in CHCl 3 Em = 415 nm Absorbance Fluorescence B1 in CHCl 3 Ex = 350 nm Ex = 312 nm Ex = 276 nm Ex = 255 nm Absorbance B2 in CHCl 3 Em = 470 nm Em = 425 nm Em = 410 nm Absorbance B2 in CHCl 3 Em = 470 nm Absorbance Fluorescence B2 in CHCl 3 Ex = 404 nm Ex = 400 nm Ex = 364 nm Ex = 311 nm
41 Absorbance B3 in CHCl 3 Em = 530 nm Em = 493 nm Em = 485 nm Absorbance B3 in CHCl 3 Em = 530 nm Absorbance Fluorescence B3 in CHCl 3 Ex = 470 nm Ex = 455 nm Ex = 433 nm Ex = 400 nm Ex = 340 nm Absorbance B4 in CHCl 3 Em = 500 nm Em = 462 nm Em = 450 nm Absorbance B4 in CHCl 3 Em = 462 nm Absorbance Fluorescence B4 in CHCl 3 Ex = 430 nm Ex = 404 nm Ex = 380 nm Ex = 365 nm
42 Absorbance B5 in CHCl 3 Em = 570 nm Em = 533 nm Em = 510 nm Absorbance B5 in CHCl 3 Em = 533 nm Absorbance Fluorescence B5 in CHCl 3 Ex = 443 nm Ex = 410 nm Ex = 385 nm Ex = 310 nm Ex = 480 nm B6 in CHCl 3 Em = 570 nm Em = 607 nm Em = 650 nm B6 in CHCl 3 Em = 570 nm Absorbance B6 in CHCl 3 Ex = 404 nm Ex = 461 nm Ex = 515nm Absorbance Absorbance Fluorescence Fig. S4. Electronic absorption excitation (left and middle panels) and fluorescence spectra of B1-B6 in CHCl 3. 42
43 B1 in CHCl 3 ; λ ex =312 nm 40 o C 0 o C -20 o C B2 in CHCl 3 ; λ ex =364 nm 40 o C 0 o C -20 o C B3 in CHCl 3 ; λ ex =430 nm 40 o C 0 o C -20 o C Fluorescence Fluorescence Fluorescence B4 in CHCl 3 ; λ ex =380 nm 40 o C 0 o C -20 o C B5 in CHCl 3 ; λ ex =445 nm 40 o C 0 o C -20 o C B6 in CHCl 3 ; λ ex =461 nm 40 o C 0 o C -20 o C Fluorescence Fluorescence Fluorescence Fig. S5. Fluorescence spectra of B1-B6 in CHCl 3 in different temperatures. 43
44 Table S1. Fluorescence wavelengths maximum of B1-B6 in CHCl 3 measured at different temperatures. B1 B2 B3 B4 B5 B6 Temperature λ max (nm) 40 o C o C o C
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