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Supporting Information for
Twisted donor–acceptor cruciform fluorophores exhibiting
strong solid emission, efficient aggregation-induced
emission and high contrast mechanofluorochromism Defang Xu,a Juanyuan Hao,b Huaizhi Gao,c Yonghui Wang,c Ying Wang,c Xingliang
Liu,c* Aixia Han,c Chao Zhangc
aState Key Laboratory of Plateau Ecology and Agriculture, Qinghai University,
Xining 810016, ChinabSchool of Materials Science and Engineering, Harbin Institute of Technology,
Harbin 150001, ChinacChemical Engineering College, Qinghai University, Xining 810016, China
*To whom correspondence should be addressed. E-mail: liuxl1219 @ 163 . com .
Table S1. Photophysical data of DMTCS-CC6 in different solvents.
solvent λabs (nm) εmax (M-1 cm-1) λem (nm) Δνsta (cm-1) Φf
b
hexane 296, 320, 423 73100 516 14404 0.132
cyclohexane 297, 321, 424 68900 518 14365 0.143
toluene 296, 321, 425 68800 548 15536 0.094
chloroform 298, 323, 426 74100 560 15700 0.073
ethyl acetate 297, 320, 426 73400 588 16663 0.023
THF 298, 322, 418 72900 593 16694 0.016
aΔνst = νabs - νem. bThe fluorescence quantum yield (Φf) was measured using quinine sulfate as a
standard (Φ = 0.546 in 0.5 mol L-1 H2SO4).
Table S2. Photophysical data of DBTCS-CC6 in different solvents.
solvent λabs (nm) εmax (M-1 cm-1) λem (nm) Δνsta (cm-1) Φf
b
hexane 297, 324, 438 71100 540 15152 0.120
cyclohexane 297, 325, 440 70000 543 15254 0.126
toluene 297, 325, 439 68200 579 16399 0.061
chloroform 296, 324, 440 69600 585 16690 0.049
ethyl acetate 297, 322, 426 76500 613 17357 0.005
THF 298, 323, 429 75800 619 17402 0.004
aΔνst = νabs - νem. bThe fluorescence quantum yield (Φf) was measured using quinine sulfate as a
standard (Φ=0.546 in 0.5 mol L-1 H2SO4).
Fig. S1 DLS data of DMTCS-CC6 (1.0×10-5 mol L-1) in THF/water (fw = 85%).
Fig. S2 DLS data of DBTCS-CC6 (1.0×10-5 mol L-1) in THF/water (fw = 85%).
Fig. S3 PL spectra of DMTCS-CC6 (a) and DBTCS-CC6 (b) in THF at different temperature
(λex = 410 nm , 1.0 × 10-5 mol L-1).
Fig. S4 Fluorescence microscopy images of DMTCS-CC6 (a) and DBTCS-CC6 (b) powders.
The excitation wavelength for measurements was 330–385 nm.
Fig. S5 Maximum fluorescent emission of DMTCS-CC6 (a) and DBTCS-CC6 (b) upon
repeating treated by grinding and fuming with CH2Cl2.
Fig. S6 1H NMR (400 MHz) spectrum of 3.
Fig. S7 1H NMR (400 MHz) spectrum of 3.
Fig. S8 13C NMR (100 MHz) spectrum of 3.
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1[c].A5
707 mV[sum= 23346 mV] Profiles 68-100 Smooth Gauss 2 -Baseline 6
Data: YP3-C44H44N2O2-632-WJZ-010001.A5[c] 17 May 2017 16:31 Cal: tof 17 May 2017 16:31 Shimadzu Biotech Axima Performance 2.9.3.20110624: Mode Reflectron_HiRes, Power: 75, Blanked, P.Ext. @ 550 (bin 48)
633.5741
577.5258
562.4237
634.6006
589.5378
605.5485
590.5427
579.5593
Fig. S9 TOF LC/MS spectrum of 3
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%Int.
626 628 630 632 634 636 638 640 642 644 646 648m/z
1[c].A5
707 mV[sum= 23346 mV] Profiles 68-100 Smooth Gauss 2 -Baseline 6
Data: YP3-C44H44N2O2-632-WJZ-010001.A5[c] 17 May 2017 16:31 Cal: tof 17 May 2017 16:31 Shimadzu Biotech Axima Performance 2.9.3.20110624: Mode Reflectron_HiRes, Power: 75, Blanked, P.Ext. @ 550 (bin 48)
633.5741
632.5431634.6006
635.6463
635.2318631.5419
Fig. S10 TOF LC/MS spectrum of 3.
Fig. S11 1H NMR (400 MHz) spectrum of DMTCS-CC6.
Fig. S12 1H NMR (400 MHz) spectrum of DMTCS-CC6.
Fig. S13 13C NMR (100 MHz) spectrum of DMTCS-CC6.
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1[c].A1
122 mV[sum= 2564 mV] Profiles 14-34 Smooth Gauss 2 -Baseline 6
Data: YP1-C62H52F6N4-966-WJZ-010001.A1[c] 17 May 2017 15:55 Cal: tof 17 May 2017 15:54 Shimadzu Biotech Axima Performance 2.9.3.20110624: Mode Reflectron_HiRes, Power: 51, Blanked, P.Ext. @ 800 (bin 51)
967.4889
968.5004
969.5111
784.2011
970.5287785.1984
Fig. S14 MALDI/TOF MS spectrum of DMTCS-CC6.
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956 958 960 962 964 966 968 970 972 974 976 978 980 982 984 986m/z
1[c].A1
122 mV[sum= 2564 mV] Profiles 14-34 Smooth Gauss 2 -Baseline 6
Data: YP1-C62H52F6N4-966-WJZ-010001.A1[c] 17 May 2017 15:55 Cal: tof 17 May 2017 15:54 Shimadzu Biotech Axima Performance 2.9.3.20110624: Mode Reflectron_HiRes, Power: 51, Blanked, P.Ext. @ 800 (bin 51)
967.4889
968.5004
969.5111
970.5287
Fig. S15 MALDI/TOF MS spectrum of DMTCS-CC6.
Fig. S16 1H NMR (400 MHz) spectrum of DBTCS-CC6.
Fig. S17 1H NMR (400 MHz) spectrum of DBTCS-CC6.
Fig. S18 13C NMR (100 MHz) spectrum of DBTCS-CC6.
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1[c].A3
199 mV[sum= 6160 mV] Profiles 1-31 Smooth Gauss 2 -Baseline 6
Data: YP2-C64H50F12N4-1102-WJZ-010001.A3[c] 17 May 2017 15:58 Cal: tof 17 May 2017 15:54 Shimadzu Biotech Axima Performance 2.9.3.20110624: Mode Reflectron_HiRes, Power: 51, Blanked, P.Ext. @ 800 (bin 51)
1103.4248
1104.4498
1105.4997
1106.5103
Fig. S19 MALDI/TOF MS spectrum of DBTCS-CC6.
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1090 1095 1100 1105 1110 1115 1120m/z
1[c].A3
199 mV[sum= 6160 mV] Profiles 1-31 Smooth Gauss 2 -Baseline 6
Data: YP2-C64H50F12N4-1102-WJZ-010001.A3[c] 17 May 2017 15:58 Cal: tof 17 May 2017 15:54 Shimadzu Biotech Axima Performance 2.9.3.20110624: Mode Reflectron_HiRes, Power: 51, Blanked, P.Ext. @ 800 (bin 51)
1103.4248
1104.4498
1105.4997
1106.5103
Fig. S20 MALDI/TOF MS spectrum of DBTCS-CC6.