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, Chapter

2. , J. =. , 2. , and J. =. , pH sensitive Layer-by-Layer film surface for bacteria growth detection H NMR (400 MHz, CD 3 OD): ?(ppm) = 1.91 (quint, 2H, J = 6.7 Hz), p.5967, 2003.

1. Hzt, 1. , and J. =. , 7.9 Hz), p.41

, To a solution of 4- hydroxybenzaldehyde (5.0 g, 40.9 mmol) in dry DMF (40 mL), K 2 CO 3 (11.3 g, 81.9 mmol) and 2-bromoethanol (6.1 g, 49.1 mmol) were added. The reaction mixture was heated to 100 °C for 1 hours with monitoring by TLC. The resulting solution was filtrated and removed the precipitate, and then extracted with ethyl acetate

1. and C. , 13 C NMR (100 MHz, NMR (400 MHz, CDCl 3 ): ?(ppm) = 4.02 (t, J = 4.1 Hz, 2H, CH 2 CH 2 ), 4.19 (t, J = 4.1 Hz, 2H, CH 2 CH 2

, Synthesis of methylnaphthyl BODIPY phenol (BODIPY-OH). A few drops of trifluoroacetic 139

, 8 g, 12.0 mmol, 2 equiv.) and 4-(2-hydroxyethoxy)-benzaldehyde (1.0 g, 6.0 mmol, 1 equiv.). The dark reaction mixture was stirred at room temperature until total disappearance of the aldehyde. The oxidising agent (chloranil, 1 equiv.), then 5 min later DIPEA (7 equiv.) and finally trifluoroborate etherate (11 equiv.) were successively added. The mixture was filtered through a pad of silica or used crude. The filtrate was, p.80

1. , 2. , and 2. , 13 C NMR (100 MHz, CDCl 3 ): ? (ppm), NMR (400 MHz, CDCl 3 ): ?(ppm) = 0.93 (m, 6H, CH 2 CH 3 3.89 (t, 2H, CH 2 CH 2 ), 4.02 (t, 2H, CH 2 CH 2 ), 6.85 (m, 2H, CH) CDCl 3 ): ?(ppm) = -126.3 (m, 0.8F), -137.3 (q, 2F, J F-B = 32.3 Hz), -147.1 (m, 0.8F). 11 B NMR (128 MHz, CDCl 3 ): ?(ppm) = -0.21 (t, J B-F = 29.5 Hz), pp.2-09631

. Synthesis, To a stirred solution of BODPY-OH (1.93 g, 2.90 mmol, 1.0 equiv.) in anhydrous CH 2 Cl 2 (58 mL) was added 4- toluenesulfonyl chloride (0.83 g, 4.34 mmol, 1.5 equiv Et 3 N (0.88 g, 8.69 mmol, 3.0 equiv.) and DMAP (0.07 g, 0.58 mmol, 0.2 equiv.) under Argon. The reaction mixture was stirred for overnight at 4 °C and quenched with a saturated aqueous NH 4 Cl (12 mL). The aqueous layer was extracted with CH 2 Cl 2 and the organic layer was washed with H 2 O, p.70

6. Chm, 2. , C. , and 2. , 13 C NMR (100 MHz, CDCl 3 ): ? (ppm) = 14, NMR (400 MHz 2H, CH 2 CH 3 ), 2.62 (s, 6H, CH 3 ), 3.73 (t, 2H, CH 2 CH 2 ), 4.09 (t, 2H, CH 2 CH 2, p.0

2. Mhzq and J. , ?(ppm) = -126.3 (m, 0.8F), -137, Hz), -147.1 (m, 0.8F). 11 B NMR (128 MHz, CDCl 3 ): ?(ppm) = -0.21 (t, J B-F = 29.5 Hz)

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, General conclusion and perspectives