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. 2023 Jan 19;66(3):1909–1927. doi: 10.1021/acs.jmedchem.2c01713

Table 3. Photochemical Properties of ortho-Halogenated Compounds.

graphic file with name jm2c01713_0011.jpg

compound R X Y n λmaxtrans (nm)a λmaxcis (nm)a λcis (nm)a λtrans (nm)a t1/2b % cis at λcisc % trans at λtransc
32a OMe F F 1 358 434 550 455 9.3 days 77 74
32b OMe Cl Cl 1 338 452 550 455 13.8 h 45 88
32c OMe F Cl 1 358 442 550 455 7.4 days 68 85
32d OMe F H 1 388 448 380 550 9.9 h 67 59
32e OMe Cl H 1 396 464 380 455 4.3 h 64 62
33a NMe2 F F 1 430   420 550 5.4 h – –
33b NMe2 Cl Cl 1 412   420 550 8.1 min – –
38a OMe F F 0 348 428 550 455 42 daysd/4.7 dayse 84 67
38b OMe Cl Cl 0 336 452 550 455 8.3 h 46 84
39f OMe F F 1 358 438 550 455 9.1 days 72 83
a

Determined by measuring UV–vis spectra at 25–100 μM in DMSO.

b

Determined by measuring UV–vis spectra at 25–100 μM in DMSO over time at room temperature after illumination with λcis.

c

Determined by HPLC at the isosbestic point of each isomeric pair (290–336 nm) after illumination of a 100 μM solution in DMSO with either λcis or λtrans.

d

Estimation, full back-isomerization not reached.

e

In DMEM with 0.1% DMSO at 37 °C, measured by HPLC.

f

With HA instead of OAA.