Appendix A. Supplementary Information. Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Appendix A Supplementary Information Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized tripodal molecular switch as a highly selective sequential ph sensor in aqueous solution Rifat Akbar 1, Minati Baral 2 and B K Kanungo 1 * 1 Department of Chemistry, Sant Longowal Institute of Engineering & Technology, Longowal, Punjab , India 2 Department of Chemistry, National Institute of Technology Kurukhestra, Haryana , India b.kanungo@gmail.com Experimental Synthesis of 1,1,1 Tris (aminomethyl)ethane (TAME) The synthesis of 1,1,1 Tris (aminomethyl)ethane (TAME) 1c was carried out under multistep reactions as detailed below: 1.1 tris[(4-tolylsulfonyl)methyl]ethane (1a) Tris(hydroxymethyl)ethane (10 g, mol) was dissolved in THF (45 ml) and added to 70 ml of aqueous solution of NaOH (16.66 g, 0.41 mol). The solution was cooled in an ice water bath and THF solution of tosyl chloride (47.66 g, 0.25 mol) was added dropwise with stirring for about 2 hours. During addition, the solution became pale yellow while an off white slurry appeared progressively; the mixture was stirred for 4 hrs further at 0 C. The reaction mixture was poured into ice water (250 ml) and extracted with toluene (3 100 ml). The combined organic phases were washed with water (2 100 ml), dried over anhydrous MgSO 4, and concentrated on rotary evaporator. The thick jelly residue was poured into methanol (500 ml) with stirring. The resulting suspension was filtered on a Buchner funnel and the precipitate was washed with water followed by methanol and diethyl ether, and dried under vacuum. The pure product was isolated as a white solid after recrystallization from
2 n propanol. Yield: 87%, mp: 105ºC. FTIR (KBr): 3023, 2954, 1889, 1686, 1605, 1478, 1458, 1367, 1302, 1290, 1153, 1099, 1012, 991, 941, 882, 805, 797, 701, 677, 532, 498 cm tris(azidomethyl)ethane (1b) Solution of tris[(4-tolylsulfonyl)methyl]ethane (1a) (25.0 g, mmol) and sodium azide (29.58 g, mmol) in dry DMSO (250 ml) was stirred under N 2 atmosphere at 125ºC for 8 hrs. The reaction mixture was poured into cold water (1.5 L), after cooling to room temperature. The aqueous solution was extracted with ethyl acetate (3 250 ml). The organic phases were washed with water (2 100 ml), dried over anhydrous NaSO 4 and reduced on a rotary evaporator. The residual oil shows strong absorption band at 2123 cm -1 in the infrared spectrum which confirms the presence of an azide and the product was used readily for the next step. 1.3 tris(aminomethyl)ethane (1c) tris(azidomethyl)ethane (1b) (21g, mmol) in freshly distilled THF(60 ml) was added to a vigrously stirred mixture of LiAlH 4 (18.63g mmol) in dry THF(300 ml) over a period of 3h under dry nitrogen. After complete addition, the mixture was refluxed for 12h, cooled, followed by addition of water (22 ml), then by NaOH (34mL of 15% aqueous solution) and again with water (50mL). The resulting slurry was stirred for 25 min and filtered through sintered glass G4 funnel under vaccum. The white residue was further refluxed over night with THF to extract remaining product. The solvent was removed from all combined filtrates to give pale yellow oil. The crude product was taken up in super dry EtOH (300mL) and concentrated HCl (12mL) was added dropwise to precipitate the compound as the trihydrochloride salt. The pure product was reprecipitated from an ethanol solution to yield a fine white powder. Yield:9.1g, 77.77mmol (72.22%), decomposes at 250 C. 1 HNMR (D 2 O) (δ): 3.24(s, 6H, 3CH 2 ) 1.20 (s, 3H,CH 3 ) hydroxyquinoline-5-methylchloride hydrochloride (2a)
3 Dry hydrogen chloride gas was passed through a solution of 8 hydroxyquinoline 2 (14.51g, 0.1 mol) and formaldehyde (20 ml, 40%) in 37% hydrochloric acid (50 ml) for 5 hours at 60 C. After filtration, the yellow solid product was washed several times with acetone and dried in vaccuo to afford 2a (14.01g) in 96.5% yield. m.p. 281 º C; 1 HNMR (300 MHz, D 2 O, 25 C, TMS): = 8.81 (d, 3 J H,H = 4.1 Hz, 1H, Ar H), 8.51 (d, 3 J H,H = 8.5 Hz, 1H, Ar H), 7.59 (dd, 3 J H,H = 8.2 Hz, 3 J H,H = 4.1 Hz, 1H, Ar H), 7.40 (d, 3 J H,H = 7.8 Hz, 1H, Ar H), 7.01 (d, 3 J H,H = 7.8 Hz, 1H, Ar H), 4.82 (s, 2H, ArCH2Cl) ppm. IR (ATR) (cm -1 ) = 3032, 2731, 1564, 1510, 1439, 1330, Elemental Analysis calcd (%) for C 10 H 9 NOCl 2 : C, 3.94 H, 6.09 N; found: C, 3.89 H, 6.13 N; MS (ES + ), m/z (I,%) = [M+1] + (90).
4 Table S1: Cartesian (X, Y, Z) coordinates of minimized structure of [(LH 9 ) +6 species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis - (methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of LH 9 : coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O O O H
5 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
6 Table S2: Cartesian (X, Y, Z) coordinates of minimized structure of [(LH 8 ) +5 species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis - (methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of LH 8 : coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O O O
7 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
8 Table S3: Cartesian (X, Y, Z) coordinates of minimized structure of [(LH 7 ) +4 species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis - (methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of LH 7 : coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O
9 O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
10 Table S4: Cartesian (X, Y, Z) coordinates of minimized structure of [(LH 6 ) +3 species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis - (methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of LH 6 : coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O
11 O O H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
12 Table S5: Cartesian (X, Y, Z) coordinates of minimized structure of [(LH 5 ) +2 species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis-(methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of LH 5 : coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O O O
13 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
14 Table S6: Cartesian (X, Y, Z) coordinates of minimized structure of [(LH 4 ) + species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis-(methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of LH 4 : coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O O O
15 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
16 Table S7: Cartesian (X, Y, Z) coordinates of minimized structure of [(LH 3 ) species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis-(methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of LH 3 : coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O O O
17 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
18 Table S8: Cartesian (X, Y, Z) coordinates of minimized structure of [(LH 2 ) - species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis-(methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of LH 2 : coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O O O
19 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
20 Table S9: Cartesian (X, Y, Z) coordinates of minimized structure of [(LH) 2- species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis-(methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of LH: coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O O O
21 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
22 Table S10: Cartesian (X, Y, Z) coordinates of minimized structure of [(L) 3- species of 5,5'- (2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)bis(azanediyl)- bis-(methylene)diquinolin-8-ol, (TAME5OX)]. XYZ file of L: coordinates in Angstrom C C C C C N N N C C C C C C C C C C C N C C C C C C C C N C C C C C C C C C C C N O O O
23 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
24 Table S11: Theoretically calculated energies (Hartrees) of (LH 9 ) +6, (LH 8 ) +5, (LH 7 ) +4, (LH 6 ) +3, (LH 5 ) +2, (LH 4 ) +1, (LH 3 ), (LH 2 ) -1, (LH) -2 and (L) -3 of TAME5OX. Species Total energy Dispersion energy Dispersion corrected energy (H 9 L) (H 8 L) (H 7 L) (H 6 L) (H 5 L) (H 4 L) (H 3 L) (H 2 L) (HL) (L) *Dispersion correction for the B3LYP functional was carried out with zero-damping, using DFTD3 V2.1 Rev 6 S. Grimme, University Muenster and coordinates from the B3LYP/ 6-31 G* optimised structures.
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