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1 Eletroni Supplementry Mteril (ESI) for Polymer Chemistry. This journl is The Royl Soiety of Chemistry 2016 Eletroni Supporting Informtion for BODIPY Bse Hyperbrnhe Conjugte Polymers for Deteting Orgni Vpors Choong Ping Sen, 1 Vng Devenr Gou, 1 Rekh Goswmi Shresth, 2 Lok Kumr Shresth, 2 Ktsuhiko Arig 2 n Suresh Vliyveettil 1* 1. Deprtment of Chemistry, 3 Siene Drive 2, Ntionl University of Singpore, Singpore. Corresponing emil: hmsv@nus.eu.sg 2. Worl Premier Interntionl Center for Mterils Nnorhitetonis (WPI-MANA), Ntionl Institute for Mterils Siene (NIMS), 1-1 Nmiki, Ibrki, Tsukub , Jpn. Tble of Contents 1. 1 H n 13 C NMR n mss spetr of monomers H NMR spetr of HP1-HP3. 3. BET nlysis of HP Absorption n emission spetr. 5. Optimize moleulr geometry of HP2 by DFT. 6. SEM imges of HP1-HP3. 7. QCM mesurement of HP2 to ifferent romti vpors.

2 1. 1 H n 13 C NMR n mss spetr of monomers Figure S1. 1 H NMR spetrum of tris-(4-ioophenyl)mine in CDCl 3. Figure S2. 1 H NMR spetrum of ompoun 2 in CDCl 3.

3 Figure S3. 13 C NMR spetrum of ompoun 2 in CDCl 3.

4 Figure S4. High resolution tmospheri-pressure hemil ioniztion mss spetrum of ompoun 2.

5 2. 1 H NMR spetr of HP1-HP3 b b Figure S5. 1 H NMR spetrum of HP1 in CDCl 3.

6 b b Figure S6. 1 H NMR spetrum of HP2 in CDCl 3. b e b e Figure S7. 1 H NMR spetrum of HP3 in CDCl 3.

7 3. BET nlysis of HP1-3 Volume bsorbe ( g -1 ) HP HP1 HP Reltive Pressure (P/P ) Surfe Are (m 2 /g) Pore Size (nm) HP HP HP Figure S8. Nitrogen sorption isotherms of HP1-3 with sorption (soli symbols) n esorption (open symbols) tres t 77 K. 4. Absorption n emission spetr Absorbne (.u) nm Compoun Wvelength (nm) Figure S9. Absorption spetrum of ompoun 2 in THF.

8 Normlize Absorbne (.u) Normlize Absorbne (.u) Normlize Absorbne (.u) 1.0 HP Wvelength (nm) 1.0 HP Wvelength (nm) 1.0 HP Wvelength (nm) Normlize Intensity (.u) Normlize Intensity (.u) Normlize Intensity (.u) 1.0 HP1 exite t 630 nm exite t 390 nm exite t 280 nm Wvelength (nm) 1.0 HP2 exite t 570 nm exite t 390 nm Wvelength (nm) 1.0 HP3 exite t 570 nm exite t 373 nm Wvelength (nm) Figure S10. Absorption (left) n emission spetr (right) of HP1-HP3 in hloroform.

9 5. Optimize moleulr geometry of HP2 by DFT Figure S11. The optimize moleulr geometry of HP2 by using DFT t B3LYP/6-311g (, p) level. Top view () n sie view (b) of HP2 moel moleule, iherl ngles of the tris(4- (5-bromo-3-hexylthiophen-2-yl)phenyl)mine (), n iherl ngles of the tris(4-(5-bromothiophen-2-yl)phenyl)mine ().

10 6. SEM imges of HP1-HP3 HP1 HP1b 2 µm 10 µm HP2 HP2b 10 µm 10 µm HP3 HP3b 10 µm 10 µm Figure S12. SEM mirogrphs of HP1-3 thin film prepre by rop-sting polymer solution in () THF, n (b) toluene on glss substrte. The solvent ws evporte slowly t room temperture.

11 7. QCM mesurement of HP2 to ifferent romti vpors. f (Hz) () time (s) Benzene Toluene o-xylene m-xylene p-xylene mesitylene f Hz (b) Benzene Toluene o-xylene m-xylene p-xylene mesitylene Figure S13. () QCM frequeny shifts of HP2 eletroe upon exposure to ifferent solvent vpors (benzene, toluene, o-xylene, m-xylene, p-xylene, n mesitylene), (b) summry of vpor sensing performne of HP2.