Supporting information for Syntheses and properties of core ...Supporting information for Syntheses...
Transcript of Supporting information for Syntheses and properties of core ...Supporting information for Syntheses...
Supporting information for
Syntheses and properties of core-substituted naphthalene
bisimides with aryl ethynyl or cyano groups
Stéphanie Chopin, Frédéric Chaignon, Errol Blart, Fabrice Odobel*
Université de Nantes, Nantes Atlantique Universités, CNRS, Faculté des Sciences et des Techniques, Laboratoire de Synthèse Organique (LSO), UMR CNRS 6513, 2, rue de la Houssinière – BP 92208 – 44322 NANTES Cedex 3 ; E-mail address : Tel : (33)-2-51-12-54-29.
Contents Figure S1: 1H NMR spectrum of 2 in CDCl3 at 298 K. Page S1 Figure S2: 13C NMR spectrum of 2 in CDCl3 at 298 K. Page S2 Figure S3: FTIR spectrum of 2 in KBr pastille at 298 K. Page S3 Figure S4: 1H NMR spectrum of 3 in CDCl3 at 298 K. Page S4 Figure S5: 13C NMR spectrum of 3 in CDCl3 at 298 K. Page S5 Figure S6: FTIR spectrum of 3 in KBr pastille at 298 K. Page S6 Figure S7: 1H NMR spectrum of 4 in CDCl3 at 298 K. Page S7 Figure S8: 13C NMR spectrum of 4 in CDCl3 at 298 K. Page S8 Figure S9: FTIR spectrum of 4 in KBr pastille at 298 K. Page S9 Figure S10: 1H NMR spectrum of 5 in CDCl3 at 298 K. Page S10 Figure S11: 13C NMR spectrum of 5 in CDCl3 at 298 K. Page S11 Figure S12: FTIR spectrum of 5 in KBr pastille at 298 K. Page S12 Figure S13: 1H NMR spectrum of 6 in CDCl3 at 298 K. Page S13 Figure S14: 13C NMR spectrum of 6 in CDCl3 at 298 K. Page S14 Figure S15: FTIR spectrum of 6 in KBr pastille at 298 K. Page S15 Figure S16: 1H NMR spectrum of 7 in CDCl3 at 298 K. Page S16 Figure S17: 13C NMR spectrum of 7 in CDCl3 at 298 K. Page S17 Figure S18: FTIR spectrum of 7 in KBr pastille at 298 K. Page S18 Figure S19: Overlay of the electronic absorption (dashed line) and emission (straight line) spectra of 4 recorded in dichloromethane. Page S19 Figure S20: Overlay of the electronic absorption (dashed line) and emission (straight line) spectra of 6 recorded in dichloromethane. Page S20 Figure S21: Overlay of the electronic absorption spectrum of 3 in pure dichloromethane (thin straight line), in dichloromethane + HPF6 (dashed line) and emission spectrum in dichloromethane + HPF6
(bold straight line). Page S21
S1
Figure S1: 1H NMR spectrum of 2 in CDCl3 at 298 K.
Ha + Hc
Hb
Hd
CH3
He
N N
O
O
O
O
Br
Br
HdHa
Hb
HcHe
CHCl3
S2
Figure S2 : 13C NMR spectrum of 2 in CDCl3 at 298 K.
N N
O
O
O
O
Br
Br
HdHa
Hb
HcHe
S3
Figure S3 : FTIR spectrum of 2 in KBr pastille at 298 K.
N N
O
O
O
O
Br
Br
HdHa
Hb
HcHe
S4
Figure S4: 1H NMR spectrum of 3 in CDCl3 at 298 K.
N N
O
O
O
O
Hm
N
N
C6H13C6H13
C6H13
Ha
Hb
Hc
Hg Hh
Hi
Hj
Hk
Hf
He
Hd
Hl
Hb + Hd
Ha + Hc
He Hl Hf
Hm
Hk
CH3
Hg - Hi
CHCl3
S5
Figure S5: 13C NMR spectrum of 3 in CDCl3 at 298 K.
N N
O
O
O
O
Hm
N
N
C6H13C6H13
C6H13
Ha
Hb
Hc
Hg Hh
Hi
Hj
Hk
Hf
He
Hd
Hl
S6
Figure S6: FTIR spectrum of 3 in KBr pastille at 298 K.
N N
O
O
O
O
Hm
N
N
C6H13C6H13
C6H13
Ha
Hb
Hc
Hg Hh
Hi
Hj
Hk
Hf
He
Hd
Hl
S7
Figure S7: 1H NMR spectrum of 4 in CDCl3 at 298 K.
Hi
Ha + Hc He + Hf + Hg Hd
Hb
Hj
CH3
N N
O
O
O
O
Hd
Hh
Hg
HfHe
Hi
Hc
Hb
Ha
HjH2O
CHCl3
S8
Figure S8 : 13C NMR spectrum of 4 in CDCl3 at 298 K.
N N
O
O
O
O
Hd
Hh
Hg
HfHe
Hi
Hc
Hb
Ha
Hj
S9
Figure S9 : FTIR spectrum of 4 in KBr pastille at 298 K.
N N
O
O
O
O
Hd
Hh
Hg
HfHe
Hi
Hc
Hb
Ha
Hj
S10
Figure S10: 1H NMR spectrum of 5 in CDCl3 at 298 K.
Hf Hg
CH3
Hd + He
Ha + Hc
Hb
N N
O
O
O
O
NC
CN
Hd
He
Hg
Hc
Hb
Ha
Hf
S11
Figure S11: 13C NMR spectrum of 5 in CDCl3 at 298 K.
N N
O
O
O
O
NC
CN
Hd
He
Hg
Hc
Hb
Ha
Hf
S12
Figure S12: FTIR spectrum of 5 in KBr pastille at 298 K.
N N
O
O
O
O
NC
CN
Hd
He
Hg
Hc
Hb
Ha
Hf
S13
Figure S13: 1H NMR spectrum of 6 in CDCl3 at 298 K.
Hf
Hg
CH3
Ha + Hc
Hb Hd
He
H2O
N N
O
O
O
O
N
N
Ha
Hb
Hc
Hg Hf
Hd
He
S14
Figure S14: 13C NMR spectrum of 6 in CDCl3 at 298 K.
N N
O
O
O
O
N
N
Ha
Hb
Hc
Hg Hf
Hd
He
S15
Figure S15: FTIR spectrum of 6 in KBr pastille at 298 K.
N N
O
O
O
O
N
N
Ha
Hb
Hc
Hg Hf
Hd
He
S16
Figure S16: 1H NMR spectrum of 7 in CDCl3 at 298 K.
N N
O
O
O
O
NC
CN
Ha
Hb
Hc
He Hd
Hd
Hb
Ha + Hc
He
CH3
CHCl3
H2O
S17
Figure S17: 13C NMR spectrum of 7 in CDCl3 at 298 K.
N N
O
O
O
O
NC
CN
Ha
Hb
Hc
He Hd
S18
Figure S18: FTIR spectrum of 7 in KBr pastille at 298 K.
N N
O
O
O
O
NC
CN
Ha
Hb
Hc
He Hd
S19
0
0,1
0,2
0,3
0,4
0,5
400 450 500 550 600 650 700
λ / nm
Abs
orba
nce
(a. u
.)
0
0,1
0,2
0,3
0,4
0,5
N N
O
O
O
O
4
Emission (a. u.)
Figure S19: Overlay of the electronic absorption (dashed line) and emission (straight line) spectra of 4 recorded in dichloromethane.
S20
0
0,1
0,2
0,3
0,4
0,5
0,6
0,7
0,8
460 510 560 610 660
λ / nm
Abs
orba
nce
(a. u
.)
0
0,1
0,2
0,3
0,4
0,5
0,6
0,7
0,8
N N
O
O
O
O
N
N
6
Emission (a. u.)
Figure S20: Overlay of the electronic absorption (dashed line) and emission (straight line) spectra of 6 recorded in dichloromethane.
S21
0
0,1
0,2
0,3
0,4
0,5
0,6
0,7
260 360 460 560 660 760
λ / nm
Abs
orba
nce
(a. u
.)
0
0,1
0,2
0,3
0,4
0,5
0,6
0,7
Emission (a. u.)
N N
O
O
O
O
N
N
C6H13C6H13
C6H13C6H13
3
Figure S21: Overlay of the electronic absorption spectrum of 3 in pure dichloromethane (thin straight line), in dichloromethane + HPF6 (dashed line) and
emission spectrum in dichloromethane + HPF6 (bold straight line).