Supporting information

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1 1 Supporting information Lilian I. Olvera, Mikhail G. Zolotukhin,*, Olivia Hernández-Cruz, Sergei Fomine, Jorge Ca rdenas, Rube n L. Gavin o-ramírez, and Fransico A. Ruiz-Trevino. Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Apartado Postal , CU, Coyoacán 04510, México D. F., México. Instituto de Química, Universidad Nacional Autónoma de Me xico, Apartado Postal , CU, Coyoacán, 04510, México D. F.,México Departamento de Ingeniería y de Ingeniería y Ciencias Químicas, Universidad Iberoamericana, Prol. Paseo de la Reforma No. 880,01219 México D.F., México. Linear, single-strand heteroaromatic polymers from superacid catalyzed stepgrowth polymerization of ketones with bisphenols Characterization. NMR spectra were recorded on Bruker Avance 400 Spectrometer, operating at and 100 MHz for 1 H and 13 C respectively. Chloroform-d (CDCl 3 ) was used as solvent. Infrared (IR) spectra were measured on a Nicolet FT-IR-ATR spectrometer. The inherent viscosities of 0.2% polymer solutions in 1-methyl-2-pyrrolidone (NMP) were measured at 25 C using an Ubbelohde viscometer. Molecular weights were determined by gel permeation chromatography (GPC MALLS) according to the published method. 1 Thermogravimetric analyses (TGA) were carried out in air and under nitrogen at a heating rate of 10 C/min on a DuPont 951 thermogravimetric analyzer. The T g was evaluated by differential scanning calorimetry (DSC) measured at 10 C/min on DuPont 910. Materials. All starting materials were obtained from Aldrich. 4,4 -Biphenol and bisphenol AF were used as received. Methylene chloride, 1,1,1-trifluoroacetone and 2,2,2-trifluoroacetophenone were distilled, isatin was purified by recrystallization with charcoal from ethanol. TFSA was distilled prior to use. Polymer Syntheses. Synthesis of polymer 1A. A mixture of 2,2,2-trifluoroacetophenone ( g, 2.4 mmol), 4,4 - dihydroxybiphenyl ( g, 2.4 mmol), TFSA (0.5 ml) and dichloromethane (3.5 ml) was stirred for 4 h at room temperature. The dark-green gel resulted was poured into methanol-water mixture then filtered and washed with hot methanol. After drying, g (98 %) of white fiber with an inherent viscosity inh of 0.82 dlg -1 (NMP) was obtained. Stoichiometric synthesis of polymer 1B. The reaction between 2,2,2-trifluoroacetophenone ( g, 2.38 mmol), bisphenol AF ( g, 2.38 mmol) into dichloromethane (2.0 ml) and TFSA (2 ml) using as solvent and catalyst, respectively, was carried out under magnetic stirring at room temperature for 7 days, then precipited and washed into water. The resulting white fiber 1.16 g (98 %) had an inherent viscosity of inh of dlg -1 in NMP.

2 2 Nonstoichiometric synthesis of polymer 1B. Reaction carried out using 2,2,2-trifluoroacetophenone ( g, 3.14 mmol), bisphenol AF ( g, 2.4 mmol), dichloromethane (2.0 ml) and TFSA (2 ml) under magnetic stirring at room temperature for 24 h. The resulting dark-brown, gel-like mass was then shredded and poured slowly into water. A white solid precipited was filtered off, washed with water and dried. The resulting polymer g (90 %) had an inherent viscosity of 0.51dL g -1 in NMP. Synthesis of polymer 2B. A mixture of 1,1,1-trifluoroacetone (1.04 g, 9.2 mmol), bisphenol AF ( g, 7.06 mmol), nitrobenzene (4.5 ml) and TFSA(0.5 ml) was stirred at room temperature for 24 h and then poured into water. The polymer was copiously washed with water and filtered off. After drying g (85 %) of beige fiber like polymer was obtained. The inherent viscosity was 0.35 dl g -1 (NMP). Synthesis of polymer 3B. A mixture of isatin ( g, 2.4 mmol), bisphenol AF ( g, 2.4 mmol) methylene chloride (1.5 ml), nitrobenzene (1.5 ml) and 1.0 ml TFSA was stirred at room temperature for 15 days and then poured into water. The white fiber formed was filtered off and washed with water several times. After drying g (93 %) the resulting white fibrous polymer had an inherent viscosity of 0.76 dl/g -1 in NMP. Figure S1. 1 H NMR spectrum of polymer 1B (in CDCl 3 ).

3 Weight (%) 3 Figure S2. 13 C NMR Spectrum of polymer 1B (in CDCl 3 ) C C Nitrogen Air Figure S3. TGA thermograms of polymer 1A.

4 Heat Flow (W/g) Weight (%) C C 60 Nitrogen 40 Air Figure S4. TGA thermograms of polymer 1B C(I) Exo Up Figure S5. DSC thermogram of polymer 1A.

5 Heat Flow (W/g) C(I) Exo Up Figure S6. DSC thermogram of polymer 1B. References 1 Cruz, A. R.; Carmen, M. G.; Guzma n-gutie rrez, M. T.; Zolotukhin, M. G.; Fomine, S.; Morales, S. L.; Kricheldorf, H. R.; Wilks, E. S.; Cardenas, J. Macromolecules 2012, 45,

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