Supporting information for Syntheses and properties of core ...Supporting information for Syntheses...
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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: 1 H NMR spectrum of 2 in CDCl 3 at 298 K. Page S1 Figure S2: 13 C NMR spectrum of 2 in CDCl 3 at 298 K. Page S2 Figure S3: FTIR spectrum of 2 in KBr pastille at 298 K. Page S3 Figure S4: 1 H NMR spectrum of 3 in CDCl 3 at 298 K. Page S4 Figure S5: 13 C NMR spectrum of 3 in CDCl 3 at 298 K. Page S5 Figure S6: FTIR spectrum of 3 in KBr pastille at 298 K. Page S6 Figure S7: 1 H NMR spectrum of 4 in CDCl 3 at 298 K. Page S7 Figure S8: 13 C NMR spectrum of 4 in CDCl 3 at 298 K. Page S8 Figure S9: FTIR spectrum of 4 in KBr pastille at 298 K. Page S9 Figure S10: 1 H NMR spectrum of 5 in CDCl 3 at 298 K. Page S10 Figure S11: 13 C NMR spectrum of 5 in CDCl 3 at 298 K. Page S11 Figure S12: FTIR spectrum of 5 in KBr pastille at 298 K. Page S12 Figure S13: 1 H NMR spectrum of 6 in CDCl 3 at 298 K. Page S13 Figure S14: 13 C NMR spectrum of 6 in CDCl 3 at 298 K. Page S14 Figure S15: FTIR spectrum of 6 in KBr pastille at 298 K. Page S15 Figure S16: 1 H NMR spectrum of 7 in CDCl 3 at 298 K. Page S16 Figure S17: 13 C NMR spectrum of 7 in CDCl 3 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 + HPF 6 (dashed line) and emission spectrum in dichloromethane + HPF 6 (bold straight line). Page S21
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).
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