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note
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Distances (Å) and angles (°) for the four unequal NH⋯O hydrogen bonds in 2: 3.05, 165; 2.80, 163; 3.02, 163; 2.76, 164, and the four equal NH ⋯O hydrogen bonds in 3: 2.84, 157. Note that the benzylic carbons in the macrocycle of 2 are slightly disordered.
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note
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8 do not exhibit dynamic NMR behavior over the temperature range of 298-203 K. It is likely that the macrocycle pirouettes around the squaraine thread, but the molecular symmetry does not allow this motion to be detected by NMR.
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14944372293
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note
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The unit cell for 2 contains four chloroform molecules, whereas 3 contains two water molecules. See Supporting Information for pictures of crystal packing and additional structural views.
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28
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0033230545
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Squaraine dyes have been considered for applications such as bioimaging probes, photosensitizers for photodynamic therapy, chemosensors, xerographic photoreceptors, photovoltaic cells, conducting polymers, and materials for nonlinear optics; see ref 2c. For more recent references, see: (a) Oswald, B.; Patsenker, L.; Duschl, J.; Szmacinski, H.; Wolfbeis, O. S.; Terpetschnig, E. Bioconjugate Chem. 1999, 10, 925. (b) Ajayaghosh, A.; Eldo, J. Org. Lett. 2001, 3, 2595. (c) Arunkumar, E.; Chithra, P.; Ajayaghosh, A. J. Am. Chem. Soc. 2004, 126, 6590. (d) Ramaiah, D.; Eckert, I.; Arun, K. T.; Weidenfeller, L.; Epe, B. Photochem. Photobiol. 2004, 79, 99.
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