Fig. 2: Synthetic route of 3a–3k, H4 and the calculated optimized geometries of 3e–3k, H4.
From: Upconversion NIR-II fluorophores for mitochondria-targeted cancer imaging and photothermal therapy
a Reagents and conditions: a (i) acetophenone, benzaldehyde, 3 M aqueous KOH, EtOH, 25 °C, 14 h, 5a: 80%; 1-(4-hydroxyphenyl)ethan-1-one: 82%; (ii) K2CO3, 3-bromoprop-1-yne, acetone, reflux 4 h, 5b: 97%; b (i) cyclopentanone, pyrrolidine, benzene, 100 °C, 4 h; (ii) compound 5, dioxane, reflux, 6 h, 6a: 68%; 6b: 66%; c thioacetic acid, boron trifluoride ether, ether, 60 °C, 2 h, 7a: 62%; 7b: 50%; d aldehydes, acetic anhydride, 70 °C, under microwave irradiation, 75 °C, 2 h, 47–60%. b Calculated optimized ground state (S0) geometries of the molecules at the B3LYP/6-31 G (d) level (Gaussian 09, Revision D.09).
