Objective To evaluate the effect of mask wearing on facial attractiveness and projected first impressions during the COVID‐19 pandemic. Methods A total of eight models were evaluated by 200 live raters and 750 online raters both with and without masks while smiling maximally. Both live and online raters looked at the models for 15 s, then completed a first impressions questionnaire. Results Overall ratings for attractiveness were higher for both masked and unmasked conditions in‐person versus online. Males were perceived more favorably both in impressions and attractiveness online when masked, whereas in person they were more favorable when unmasked. Females were perceived more favorably in impressions when unmasked both online and in person, but their attractiveness rating was higher when masked both online and in person. Regardless of gender and masking state, all first impressions were more favorable in person versus online. The differences were statistically significant (all p < 0.05). Conclusions Face masks have different effects for males versus females in both an online and in‐person setting. Men are perceived more positively in‐person when they smile unmasked while they are better ranked online when they smile masked. Females are better perceived in all domains other than attractiveness when smiling unmasked both online and in person. To optimize first impressions, individuals should seek to meet in person whenever possible when forming new relationships.

The title compound, C24H30Br2N4O2, consists of a 2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine entity with a 12-bromododecyl substituent attached to the pyridine N atom. The middle eight-carbon portion of the side chain is planar to within 0.09 (1) Å and makes a dihedral angle of 21.9 (8)° with the mean plane of the imidazolopyridine moiety, giving the molecule a V-shape. In the crystal, the imidazolopyridine units are associated through slipped π–π stacking interactions together with weak C—HPyr...ONtr and C—HBrmdcyl...ONtr (Pyr = pyridine, Ntr = nitro and Brmdcyl = bromododecyl) hydrogen bonds. The 12-bromododecyl chains overlap with each other between the stacks. The terminal –CH2Br group of the side chain shows disorder over two resolved sites in a 0.902 (3):0.098 (3) ratio. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (48.1%), H...Br/Br...H (15.0%) and H...O/O...H (12.8%) interactions. The optimized molecular structure, using density functional theory at the B3LYP/ 6–311 G(d,p) level, is compared with the experimentally determined structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

In the title molecule, C20H24Br2N4, the imidazopyridine moiety is not planar as indicated by the dihedral angle of 2.0 (2)° between the constituent rings; the 4-dimethylaminophenyl ring is inclined to the mean plane of the imidazole ring by 27.4 (1)°. In the crystal, two sets of C—H...π(ring) interactions form stacks of molecules extending parallel to the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (42.2%), H...C/C...H (23.1%) and H...Br/Br...H (22.3%) interactions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 2.3591 eV.

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