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, HRMS (ESI + ) m/z calc

, amino-2-oxoethyl)azanediyl)bis(ethane-2,1-diyl))bis

, Pd/C (29 mg, 30 % wt) in methanol (15 mL). 53 was obtained as a yellow oil, vol.67

, %) and the crude product was used for the next step without further purification

. Tlc-(sio2, /. Ch2cl2, and . Meoh,

H. Nmr, 300 MHz, CDCl3) ? (ppm): 3.99 (s, 2H, H 4 )

C. Nmr, 75 MHz, CDCl3) ? (ppm): 170.6 (CIV CONH2), 167.8 (C 12 ), vol.167

, (dimethylamino)-2-oxoethyl)azanediyl)bis(ethane-2,1627 mg, 1.92 mmol), glycinedimethylamide (98 mg, 0.96 mmol) and K2CO3 (1.324 g, 9.6 mmol) in anhydrous CH3CN (45 mL). The crude product was purified by column chromatography (Al2O3, CH2Cl2/MeOH: 99/01 to 95/05) to give 54 as a yellow oil

. Tlc-(sio2, /. Ch2cl2, and . Meoh,

H. Nmr, 75 (s, 4H, 300 MHz, CDCl3) ? (ppm): 7.35-7.20 (m, 10H, H 13 , H 14 , and H 15 ), vol.3

C. Nmr, MHz, CDCl3) ? (ppm): 170.68 and 170.66 (C 3 and C 8 ), 139.0 (C 12 ), vol.128

, dimethylamino)-2-oxoethyl)azanediyl)bis(ethane-2,1-diyl

, Pd/C (51 mg, 30 % wt) in methanol (15 mL). 55 was obtained as a yellow oil, vol.105

, %) and the crude product was used for the next step without further purification

. Tlc-(sio2,

H. Nmr, 22 (s, 4H, H 7 ), 2.98 (s, 3H, H 1 ), 2.84 (s, 3H, 300 MHz, CDCl3) ? (ppm): 3.39 (s, 2H, H 4 ), vol.3

C. Nmr, 75 MHz, CDCl3) ? (ppm): 170.7 (C 3 ), vol.168

, 22 mmol, 1 eq) and carbostyrile 62 (50 mg, 0.22 mmol, 1 eq) in DMSO (2 mL) was added triethylamine (207 µL, 0.77 mmol, 3.5 eq) and HBTU (582 mg, 0.77 mmol, 3.5 eq), then the mixture was stirred at room temperature for 24h. The reaction was stopped with H2O (3 mL) then CH2Cl2 (10 mL) was added. The organic layer was successively washed with NaOH (1M), H2O, NH4Cl (sat.) and H2O, then dried over MgSO4, filtered and the solvent was removed in vacuo, vol.19

. Tlc-(al2o3, /. Ch2cl2, and . Meoh,

H. Nmr, 500 MHz, MeOD) ? (ppm): 8.32 (d, 5 J H-H = 2.1 Hz, 1H, H 11 ), 7.83 (dq, p.3

, Hz and 5 JH-H = 2.1 Hz, 1H, H 8 ), 7.73 (s, 2H, H15), 7.55 (dd, 3 JH-H = 9.0 Hz and 5 JH-H =

1. Hz, JA-B = 14.8 Hz, A part of an AB system, 2H, H 17 ), 3.84 (d, JA-B = 14.8 Hz, B part of an AB system, 2H, H 17 ), 3.56 (d, JA-B = 17.5 Hz, A part of an AB system, 2H, H 20 ), 3.46 (d, JA-B = 17.5 Hz, B part of an AB system, vol.2

C. Nmr, MeOD) ? (ppm): 173.3 (C 25 ), 172.8 (C 21 ), MHz, vol.165, issue.126

, 122.6 (q, 1 JC-F = 274.5 Hz, C 1 ), 119.0 (C 15 ), 118.8 (q, 3 JC-F = 5.5 Hz, C 3 ), vol.115

F. Nmr, 282 MHz, MeOD) ? (ppm):-64, vol.85

, HRMS (ESI+) m/z (%)

, HRMS (ESI+) calcd

. Py-hbim,

, IR (cm-1 ) KBr pellet: 2977, 1155.

, MS (ESI+) m/z (%): 578, vol.4

. Tlc-(al2o3,

H. Nmr, 71 (s, 8H, H 6 ), 3.30 (s, 4H, H 13 ), 3.23 (s, 8H, 300 MHz, CDCl3) ? (ppm): 6.82 (s, 4H, H 3 ), vol.3

C. Nmr, CDCl3) ? (ppm): 170.8 (C 14 ), MHz, vol.170, issue.75

, IR (cm-1 ) KBr pellet: 2977, 1156.

, MS (ESI+) m/z (%): 1155.7 (100)

H. Ligand,

, Macrocycle H3L8 was obtained as described above for macrocycle H3L7 from 69 (85 mg, 127 ?mol)

H. Nmr, 300 MHz, D2O) ? (ppm): 7.95 (s, 2H, H 11 )

C. Nmr, 75 MHz, D2O) ? (ppm): 174.7 (C 19 ), vol.168, p.15

, 127.5 (C 4 and C 5 ), vol.119

, ESI-) m/z (%): 519.1964 (30), HRMS

, HRMS (ESI-) calcd

, Ligand H4L9, vol.6, pp.13-16

, Macrocycle 71 (100 mg, 0.173 mM)

H. Nmr, A part of an AX system, 300 MHz, D2O) ? (ppm): 7.28 (s, 2H, H 3 ), 4.98 (d, JA-X = 13.4 Hz, vol.2

C. Nmr, D2O) ? (ppm): 175.0 (C 12 ), 168.8 (C 8 ), MHz, vol.150, issue.75, p.133

, MS (ESI+) m/z (%)

, HRMS (ESI+) m/z (%), pp.448-462

, HRMS (ESI+) calcd

H. Ligand,

, The hexaester 72 (100 mg, 0.087 mmol) was stirred in a mixture of CH2Cl2 (5 mL) and

H. Nmr, 300 MHz, D2O) ? (ppm): 7.21 (s, 4H, H 3, vol.2

C. Nmr, D2O) ? (ppm): 174.2 (C 12 ), 170.2 (C 8 ), MHz, vol.152, issue.75

, IR (cm-1 ) KBr pellet: 3405, vol.3008, 1205.

, HRMS (ESI+) m/z (%): 841.3 (100)

, HRMS (ESI+) calcd

, Luminescence ?em (Tris buffer, pH 7.4, ?ex = 282 nm)/nm: 489 (relative intensity, p.621

]. Eu, UPLC analysis: tR = 3.79 min (System 1), purity 88%

E. C20h24n4o8eu, m/z = 601.0808 ( 153 Eu) and m/z = 599.0793