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1 Supporting Information Distinct Mechanoresponsive Luminescence, Thermochromism, Vapochromism and Chlorine Gas Sensing by a Solid-State Organic Emitter S1
2 Figure S1. 1 H NMR (in CDCl 3 ) spectra of as synthesized 1. S2
3 Figure S2. 13 C NMR (in CDCl 3 ) spectra of as synthesized 1. S3
4 Figure S3. High resolution mass spectra (HRMS) of (a) 1O and (b) 1Y. Calculated [M+H] is S4
5 Figure S4. TGA plots of 1Y and 1O crystals. Figure S5. DSC traces of (a) 1Y crystal and (b) 1O crystal. S5
6 Figure S6. (a) Normalized UV-Vis and (b) fluorescence spectra of 1 in different solvents. Figure S7. DFT calculated frontier molecular orbitals (FMO) of 1 in polar(acetone) and nonpolar (hexane) solvents. S6
7 Figure S8. (a) Solid state excitation spectra of the 1Y and 1O crystals. (b, c) Excitation wavelength dependent emission of 1Y and 1O crystals shows red shift of the emission band at higher wavelength excitation. (d). Excitation spectra of 1O crystal by monitoring emission at different wavelengths. S7
8 Figure S9. (a, b) Fluorescence microscope pictures of PMMA and agarose hybrid films of 1. (c) Drop-casted film (from CHCl 3 solution 1x 10-3 M), (d) Corresponding fluorescence spectra of all the films. Figure S10. Experimental PXRD plots. (a) Full range experimental PXRD plots of 1O-grind, 1Y-grind samples and isolated green emissive form. (b, c, d) Expanded regions showing slight difference in PXRD pattern of the samples. S8
9 Figure S11. Various Intermolecular interactions in 1O crystal. Red dotted line is denoted for H bonding interaction, green dotted line is for C H interaction. Figure S12. (a) Unit cell packing of 1O. (b) Cartoon representation of possible molecular arrangements in different emissive solid forms of 1. S9
10 Figure S13. IR spectra at different stages of grinding. (a) ATR spectra of 1O crystal (orange line) and IR Spectra (KBr powder matrix) of the 1O-gently crushed (blue line), and 1O-hard grinded (green line). (b) Expanded plot of C H in plane bending frequency region, (c) C H stretching frequency region and (d) C N stretching frequency region. S10
11 Figure S14. (a) Raman spectra of the crystals and hard grinded film showing slight change in Ar C F frequency upon grinding (b) UV-Vis spectra of 1O-grinded film (on quartz plate) (c) Excitation wavelength dependent emission of 1O-grinded film. (d) Fluorescence excitation spectra at different stages of grinding of 1Y crystal. Note, the band at 515 nm that correspond to intermolecular interactions gradually disappear in the course of grinding. Figure S15. Solid state emission decay profiles. (a) 1Y crystal, (b) 1O crystal, (c) 1O-gently crushed material, (d) 1O-hard grinded material. S11
12 Figure S16. BDFH surface analysis and packing orientation of 1O crystal. Figure S17. Luminescence shift of 1Y-grinded film upon exposure to ethyl acetate vapour. (a) Fluorescence microscope images. (b) Corresponding fluorescence spectra. S12
13 Figure S18. Luminescence shift of 1O-grinded film upon exposure to ethyl acetate vapour. (a) Fluorescence microscope images. (b) Corresponding fluorescence spectra. Figure S19. Fluorescence microscopic snapshots of PL change of 1Y-crystal upon thermal heating and melting. The picture of melt crystal at 125 C was taken under visible light since it was non-fluorescent. S13
14 Figure S20. Photoluminescence & crystallinity switching of 1Y- melt (melt solid cooled to RT) upon exposure to acetone vapour at RT. (a) Fluorescence microscope image of 1Ymelt. (b) 1Y-melt after exposure to acetone vapour. (c) PXRD patterns before and after acetone vapour exposure. (d) Emission profiles at different stages of acetone vapor exposure. S14
15 Figure S21. (a) Fluorescence microscopic snapshots of 1O crystal upon thermal heating and melting. (b) Corresponding PXRD pattern of melt (recorded at 130 C) and cooled solid (recorded at 30 C). Figure S22. Plot for the concentration of Cl 2 gas vs fluorescence intensity of 1Y-grinded film. S15
16 Figure S23. IR spectra of 1Y-grinded powder (in KBr) before and after 5 mins of exposure to chlorine gas (evolved from bleaching powder and water). Figure S24. PXRD of 1Y-grind powder before and after 5 mins of exposure to chlorine gas (evolved from bleaching powder and water). S16
17 Figure S25. Fluorescence intensity change upon purging Cl 2 gas (from bleaching powder and water) in chloroform solution of 1. S17
18 Figure S26. 1 HNMR spectra of 1 in CDCl 3 before and after purging Cl 2 gas that was generated from bleaching powder and water. (a) Before chlorine purging. (b) 1 minute of purging, (c) 10 minutes of purging. (d) Keeping at RT for 48 hours after Cl 2 purging. S18
19 Figure S27. ESI Mass spectra after exposure (30 min) of 1 to chlorine gas (from bleaching powder). Table S1. Solid state emission maxima and quantum yield ( ) of the crystals. Compound em, max / nm 1 (in CHCl 3 ) Y O S19
20 Table S2. Single crystal X-ray diffraction parameters of 1O at 293K 1O (293 K) Chemical formula C 27 H 18 F 2 N 2 M r Crystal system Triclinic Space group P ī a / Å (2) b / Å (3) c / Å (8), (10), (10) (10) V / Å (14) Z 6 ρ calc / (g cm 3 ) μ / mm F θ min / 2.16 θ max / Reflections collected Independent reflections 6287 GoF Final R indices R 1 = , [I > 2σ(I)] R indices (all data) wr 2 = R 2 = , wr 2 = S20
21 Table S3. Intermolecular interactions in 1O crystal (at 293 K). Intermolecular Interactions Hydrogen bonding interactions D H A angle / H A / D A distance / Å C26 H26 F / 3.399(3) C46 H46 F / 3.238(3) C15 H15 N / 3.259(4) Other intermolecular interactions C44 N along b-axis C H79 centroid) along b-axis C25 H25 centroid) Approx. along c-axis C H19 centroid) Table S4. Twist angles between different phenyl planes. Three values in each case corresponds to three molecules in asymmetric unit. Angles / 1O <p1-p , 81.78, <p3-p , 44.66, <p3-p , 60.62, <p3-p , 62.40, Table S5. Solid state life time ( ) values of the crystals and grinded materials Compounds Life time, / ns 1 (in CHCl 3 ) 1 = = O crystal (orange emissive) 1 = (36.06 %) S21
22 ex = 405 nm, em = nm 2 = (27.55 %) 3 = (36.37 %) 2 = O-gentle grinded ex = 405 nm, em = nm 1 = (57.65 %) 2 = (23.99 %) 3 = (18.32 %) 2 = O-hard grinded ex = 405 nm, em = nm 1 = (58.05 %) 2 = (27.04 %) 3 = (14.94 %) 2 = Y crystal ex = 405 nm, em = nm 1 = (69.11 %) 2 = (10.19 %) 3 = (20.69 %) 2 = 1.10 Table S6. Geometry optimized (gas phase) coordinate of S22
23 S23
24 End of SI. S24
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