8 (a) A. Go´mez-Hens and M. P. Aguilar-Caballos, Trends Anal. Chem.,
2004, 23, 127; (b) K. Szaciłowski, W. Macyk, A. Drzewiecka-Matuszek,
M. Brindell and G. Stochel, Chem. Rev., 2005, 105, 2647.
(500 MHz, CDCl3): 8.11–8.00 (m, 8H), 7.51–7.35 (m, 6H), 7.04 (s, 2H),
6.99 (d, J = 9.0, 4H), 4.25 (t, J = 6.4, 4H), 3.32–3.17 (m, 16H), 2.98
(t, J = 7.3, 4H), 2.42–2.28 (m, 4H), 1.61 (dt, J = 12.0, 7.8, 16H),
1.51–1.31 (m, 16H), 0.98 (t, J = 7.3, 24H). dC (100 MHz, CDCl3):
161.7, 158.0, 145.2, 142.9, 132.5, 131.6, 129.21, 129.18, 128.5, 123.7,
118.6, 114.8, 67.4, 58.7, 48.2, 25.6, 23.9, 19.7, 13.7. HRMS (ESI) calcd
for C38H33BN3O8F2S2 [M - H+]- 772.1770, found 772.1757. IR (KBr
disc) cm-1: 1468, 1505, 1603.
9 (a) J. Killoran, L. Allen, J. F. Gallagher, W. M. Gallagher and D. F.
O’Shea, Chem. Commun., 2002, 1862; (b) A. Gorman, J. Killoran, C.
O’Shea, T. Kenna, W. M. Gallagher and D. F. O’Shea, J. Am. Chem.
Soc., 2004, 126, 10619; (c) S. O. McDonnell, M. J. Hall, L. T. Allen, A.
Byrne, W. M. Gallagher and D. F. O’Shea, J. Am. Chem. Soc., 2005, 127,
16360; (d) W. M. Gallagher, L. T. Allen, C. O’Shea, T. Kenna, M. Hall,
J. Killoran and D. F. O’Shea, Br. J. Cancer, 2005, 92, 1702; (e) M. J.
Hall, S. O. McDonnell, J. Killoran and D. F. O’Shea, J. Org. Chem.,
2005, 70, 5571; (f) A. T. Byrne, A. O’Connor, M. Hall, J. Murtagh,
K. O’Neill, K. Curran, K. Mongrain, J. A. Rousseau, R. Lecomte, S.
McGee, J. J. Callanan, D. F. O’Shea and W. M. Gallagher, Br. J. Cancer,
2009, 101, 1565.
10 (a) J. Killoran and D. F. O’Shea, Chem. Commun., 2006, 1503; (b) M. J.
Hall, L. T. Allen and D. F. O’Shea, Org. Biomol. Chem., 2006, 4, 776;
(c) S. O. McDonnell and D. F. O’Shea, Org. Lett., 2006, 8, 3493; (d) R. E.
Gawley, H. Mao, M. Mahbubul Haque, J. B. Thorne and J. S. Pharr,
J. Org. Chem., 2007, 72, 2187; (e) A. Coskun, M. Deniz Yilmaz and
E. U. Akkaya, Org. Lett., 2007, 9, 607; (f) A. Loudet, R. Bandichhor, L.
Wu and K. Burgess, Tetrahedron, 2008, 64, 3642; (g) J. Killoran, S. O.
McDonnell, J. F. Gallagher and D. F. O’Shea, New J. Chem., 2008, 32,
483.
13 Synthesis of 12. Compound 11 (300 mg, 0.41 mmol) was dissolved in
dry CH2Cl2 (60 mL), treated with methyl iodide (260 mL, 4.1 mmol)
and stirred under N2 for 24 h at rt. The solvent was removed under
reduced pressure and recrystallisation from CH2Cl2–Et2O (8 : 1) gave
the product 12 (330 mg, 80%) as a dark green solid mp > 300 ◦C. dH
(500 MHz, DMSO-d6): 8.30 (d, J = 8.0 Hz, 4H), 8.20 (d, J = 9.0 Hz,
4H), 7.77 (d, J = 8.0 Hz, 4H), 7.74 (s, 2H), 7.17 (d, J = 9.0 Hz, 4H),
4.62 (s, 4H), 3.90 (s, 6H), 3.43–3.39 (m, 4H), 3.31–3.26 (m, 4H), 2.95 (s,
6H), 1.35 (t, J = 7.0 Hz, 12H). dC (125 MHz, DMSO-d6): 162.7, 158.1,
145.1, 141.2, 133.8, 132.4, 129.7, 129.4, 123.4, 121.0, 115.0, 63.5, 56.1,
55.8, 46.6, 8.30. IR (KBr disc) cm-1: 3434, 1603. ES-MS: m/z 884.7
[M - I-]+. HRMS (ESI) calcd for C46H54BF2IN5O2 [M - I-]+ 884.3383,
found 884.3381.
14 Due to lack of solubility in organic solvents the data was collected on
bis-tetrabutylammonium salt.
15 As would be expected aggregration was observed in water alone, for
examples of this with cyanine and methylene blue dyes see: (a) T. D.
Slavnova, H. Go¨rner and A. K. Chibisove, J. Phys. Chem. B, 2007, 111,
10023; (b) J. Jose, Y. Ueno and K. Burgess, Chem.–Eur. J., 2009, 15,
418.
11 J. Murtagh, D. O. Frimannsson and D. F. O’Shea, Org. Lett.,
DOI: 10.1021/ol902140v.
12 Synthesis of 8. Compound 7 (168 mg, 320 mmol), propane-1,3-sultone
(97 mg, 800 mmol) and K2CO3 (110 mg, 800 mmol) were heated
under reflux in acetone (60 mL) for 6 h, under a N2 atmosphere.
The resulting precipitate was filtered, washed with acetone and cold
methanol. Preparative RP-HPLC (C-18; acetonitrile–water, 60 : 40;
retention time: 3 min) afforded 7 (102 mg, 41%) as a green solid
m.p. > 300 ◦C. For, NMR analysis the compound was transformed into
tetrabutylammonium salt by extraction of aqueous solution of 8 with
CHCl3 in presence of tetrabutylammonium chloride. The organic phase
was washed with water twice, dried and evaporated. dH of 8·(NBu4)2
16 Their strong absorption at 633 nm corresponds to HeNe laser excitation
wavelength and emission profile matches with the use of 650 nm long-
pass filters.
17 R. Artali, G. Bombieri, L. Calabi and A. D. Pra, Farmaco, 2005, 60,
485.
18 (a) M. J. Luetkemeier and J. A. Fattor, Clin. Chem., 2001, 47, 1843;
(b) M. L. Landsman, G. Kwant, G. A. Mook and W. G. Zijlstra, J. Appl.
Physiol., 1976, 40, 575.
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