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1 Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2017 Electronic supplementary information for Highly responsive ethylenediamine vapor sensor based on perylenediimide camphorsulfonic acid complex via ionic self-assembly Yongwei, Huang, a Xiaotian, Liu, a,b Qing Wang c Jiya Fu, b,* Lili Zhao, c,* Zhonghua Liu a,* and Dongzhu Jin a a Laboratory of Nanomedicine, School of Basic Medical Science, Henan University, Kaifeng , China. b Henan Engineering Laboratory of Flame-Retardantand Functional Materials, School of Chemistry and Chemical Engineering, Henan University, Kaifeng, , China c Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing , China
2 1. Synthesis of PR and PS N,N -Bis(2-(dimethylammoethyl)perylene-3,4,9,10-tetracarboxyldiimide (2) 3,4:9,10-perylenedicarboximide (2.00 g, 5 mmol) and N, N'- dimethylethylenediamine (7.05 g, 80 mmol) was stirred in 20 ml 1-benzazine for 24 h at 160 o C under argon atmosphere. The mixture was cooled to room temperature, subsequently added 50 ml CH 3 OH into the mixture, then stirred overnight and filtered, and dried in vacuum at 60 o C to give dark red 2 (2.40 g). This product was used in the next step without further purification. N,N -Bis(2-(trimethylammoniumiodide)ethylene)perylene-3,4,9,10- tetracarboxyldiimide iodide (PDI-I) 2 (1.33 g, 2.5 mmol) and iodomethane (2.84 g, 20 mmol) was stirred in methylbenzene (80 ml) for 6 h at 100 o C. The mixture was cooled to room temperature, stirred overnight and filtered, washed with ether, and dried in vacuum at 60 o C to give dark red PDI-I (1.55 g, 76 %). 1 H NMR (400 MHz, DMSO-d 6 ): δ 8.66 (d, 4 H, J = 8 Hz), 8.40 (d, 4 H, J = 8 Hz), (m, 4 H), (m, 4 H), (m, 18 H). N,N -bis(2-(trimethylammoniumethylene)perylene-3,4,9,10- tetracarboxyldiimide-(r)-(-)-camphorsulfonic acid salt (PR) 3 (0.05 g, 0.06 mmol) and (R)-(-)-camphorsulfonic acid (0.14 g, 0.60 mmol) was
3 stirred in CH 3 OH (20 ml) for 24 h at 70 o C, then methylbenzene (150 ml) was added, the mixture was stirred overnight. The precipitate was recovered by filtration, dried in vacuum at 60 o C. This solid was further purified by recrystallization with ethanol to give the dark red solid (0.04 g, 65.03%). 1 H NMR (400 MHz, DMSO-d 6 ): δ 9.02 (d, 4 H, J = 8 Hz), 8.65 (d, 4 H, J = 8 Hz), 4.51 (m, 4 H), 3.66 (m, 4 H), 3.24 (s, 18 H), 2.85 (d, 2 H J = 16 Hz), 2.70 (m, 4 H), 2.35 (d, 2 H J = 16 Hz), 2.25 (m, 1 H), 2.21 (m, 1 H), 1.93 ( m, 2 H), 1.79 ( m, 2 H), 1.25 ( m, 4 H), 1.02 ( s, 6 H), 0.74 ( s, 6 H). Anal. Calcd for C 54 H 64 N 4 O 12 S 2 : C, 63.26; H, 6.29; N, 5.46; S, Found: C, 63.29; H, 6.24; N, 5.38; S, N,N -bis(2-(trimethylammoniumethylene)perylene-3,4,9,10- tetracarboxyldiimide-(s)-(+)-camphorsulfonic acid salt (PS) 3 (0.05 g, 0.06 mmol) and (1S)-(+)-10-camphorsulfonic acid (0.14 g, 0.60 mmol)was stirred in CH 3 OH (20 ml) for 24 h at 70 o C, then methylbenzene (150 ml) was added, the mixture was stirred overnight. The precipitate was recovered by filtration, dried in vacuum at 70 o C. This solid was further purified by recrystallization with ethanol to give the dark red solid (0.05 g, 83.33%). 1 H NMR (400 MHz, DMSOd 6 ): δ 8.86 (d, 4 H, J = 8 Hz), 8.54 (d, 4 H, J = 8 Hz), 4.51 (m, 4 H), 3.68 (m, 4 H), 3.26 (s, 18 H), 2.86 (d, 2 H J = 16 Hz), 2.68 (m, 4 H), 2.36 (d, 2 H J = 16 Hz), 2.25 (m, 1 H), 2.21 (m, 1 H), 1.93 ( m, 2 H), 1.79 ( m, 2 H), 1.25 ( m, 4 H), 1.04 ( s, 6 H), 0.73 ( s, 6 H). Anal. Calcd for C 54 H 64 N 4 O 12 S 2 : C, 63.26; H, 6.29; N, 5.46; S, Found: C, 63.31; H, 6.27; N, 5.42; S, 6.20.
4 2. Supporting Figures and Table Table S1 The dipole moment of the liquid analytes tested 1 and the corresponding increment of current measured at concentration of 100 ppm. analytes μ (D) Current (PS/PR, μa) ethylenediamine 1.99± /0.016 hydrazine 1.75± /0.004 ammonia ± /0.003 ethylamine 1.22± /0.001 butylamine 1.0 -/- triethylamine 0.66±0.05 -/- diethylamine 0.92±0.05 -/- aniline 1.13±0.02 -/- Table S2. The average hydrogen-bonding distances (in Å) in PR and PS monomers and dimers (in bracket) at the different computational levels PR PS H-bond avg H-bond avg monomer dimer monomer dimer AM HF/6-31G(d, p) BP86/def2-SVP BP86-(D3BJ)/def2-SVP Table S3. Dimerization energies ΔE(dimerization) (in kcal/mol) at the different computational levels. Methods PR dimer PS dimer AM HF/6-31G(d, p) BP86/def2-SVP RI-BP86-(D3BJ)/def2-SVP
5 Fig. S1 Schematic diagram of device fabrication by using organic ribbon mask technique; the dashed line in Stage 2 shows the selected nanofiber using to prepare the sensing device in next stage. Fig. S2 Schematic diagram for the vapor sensing measurement system. Fig. S3 Responses of PDI-I devices in ethylenediamine vapor (100 ppm).
6 Fig. S4 The absorption spectra of PR and PS films in air and in ethylenediamine vapor (100 ppm). Fig. S5 UV-vis spectra of PDI-I in air and in ethylenediamine (100 ppm). (a) PR monomer (b) PS monomer Fig. S6 Optimized structures of (a) PR monomer, and (b) PS monomer at the AM1 level. The average hydrogen bond distances are in Å. The color code, N: blue, O: red, C: gray, H: white.
7 (a) PR monomer (b) PS monomer Fig. S7 Optimized structures of (a) PR monomer, and (b) PS monomer at the HF/6-31G(d,p) level. The average hydrogen bond distances are in Å. The color code, N: blue, O: red, C: gray, H: white. (a) PR monomer (b) PS monomer Fig. S8 Optimized structures of (a) PR monomer, and (b) PS monomer at the bp86/def2-svp level. The average hydrogen bond distances are in Å. The color code, N: blue, O: red, C: gray, H: white.
8 (a) PR dimer (b) PS dimer Fig. S9 Optimized structures of (a) PR dimer, and (b) PS dimer at the AM1 level. The average hydrogen bond distances are in Å. Dimerization energies ΔE(dimerization) are in kcal/mol. The color code, N: blue, O: red, C: gray, H: white. (a) PR dimer
9 (b) PS dimer Fig. S10 Optimized structures of (a) PR dimer, and (b) PS dimer at the AM1 level. The average hydrogen bond distances are in Å. Dimerization energies ΔE(dimerization) are in kcal/mol. The color code, N: blue, O: red, C: gray, H: white. (a) PR dimer (b) PS dimer Fig. S11 Optimized structures of (a) PR dimer, and (b) PS dimer at the AM1 level. The average hydrogen bond distances are in Å. Dimerization energies ΔE(dimerization) are in kcal/mol. The color code, N: blue, O: red, C: gray, H: white.
10 SI x. Coordinates and energies (kcal/mol) of the calculated structures at the BP86-D3(BJ)/def2-SVP level PR-monomer Energy = C C C C C C C C C C C N C O O C C N C C C C C C C C C C C C C S O O O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C C C C C C C C C C C N C O
11 O C C N C C C C C C C C C C C C C S O O O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H PS-monomer Energy = C C C C C C C C C C C C C C C C C C C C C N C C N C O O O O C
12 C N C C C N C C C C C C C C C C C C C C C S O O O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C C C C C C C C C C S O O
13 O O H H H H H H H H H H H H H H H PR-dimer Energy = C C C C C C C C C C C N C O O C C N C C C C C C C C C C C C C S O O O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
14 H C C C C C C C C C C C N C O O C C N C C C C C C C C C C C C C S O O O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C C C C C C C C C C C N C O O C C N C
15 C C C C C C C C C C C C S O O O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C C C C C C C C C C C N C O O C C N C C C C C C C C C C C C C S O O O O H H H
16 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H PS-dimer Energy = C C C C C C C C C C C C C C C C C C C C C N C C N C O O O O C C N C C C N C C C C C C C C C C C C C C C S O O O
17 O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C C C C C C C C C C S O O O O H H H H H H H H H H H H H H H C C C C C C C C
18 C C C C C C C C C C C C C N C C N C O O O O C C N C C C N C C C C C C C C C C C C C C C S O O O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
19 H H H H H H H H H H C C C C C C C C C C S O O O O H H H H H H H H H H H H H H H References 1 W. M. Haynes, CRC Handbook of Chemistry and Physics, 91st ed; CRC Press: Boulder, CO, USA,
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