1 indanone

1-Indanone (1-INO), 1H-phenalen-1-one (1H-PHO), acenaphthylene-1,2-quinone (1,2-ACNQ), chrysene-1,4-quinone (1,4-CHRQ), 2-methylanthracene-9,10-quinone (2-MAQ), 2,3-dimethylanthracene-9,10-quinone (2,3-DMAQ), naphthacene-5,12-quinone (5,12-NQ), 7H-benz[de]anthracene-7-one (7H-BAO), 9-fluorenone (9-FLO), phenanthrene-9,10-quinone (9,10-PQ), anthracene-9,10-quinone (9,10-AQ) and benz[a]anthracene-7,12-quinone (7,12-BAQ) all with purity ≥95% and from Sigma Aldrich (Stockholm, Sweden) were kindly provided by Dr Staffan Lundstedt at Umeå University. 4H-Cyclopenta[def]phenanthrene-4-one (4H-CPO), benzo[a]fluorenone (BFLO) and 6H-benzo[cd]pyren-6-one (6H-BPO), all with purity ≥99% were obtained from the Institute for Reference Materials and Measurements (EC-JRC-IRMM, Geel, Belgium). 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD; CASRN 1746-01-6, 98%) was obtained from Cambridge Isotope Laboratory (Andover, MA). Benzo[a]pyrene (B[a]P; CASRN 50-32-8, ≥96%), 7-ethoxyresorufin, fluorescamine, dihydronicotinamide-adenine dinucleotide phosphate (NADPH) and microsomes containing recombinant human CYP1A1 and NADPH-P450 reductase were obtained from Sigma-Aldrich (Stockholm, Sweden). All cell culture reagents were purchased from Gibco (Life Technologies, Stockholm, Sweden).

The
reagents zinc acetate dihydrate (Zn(OAc)₂.2H₂O), terephthalic acid (H₂bdc), 4,4′-biphenyldicarboxylic
acid (H₂bpdc), aluminum chloride, acetyl chloride, 1,3,5-triphenylbenzene,
sodium hydroxide (NaOH), anhydrous magnesium sulfate (MgSO₄), bromine, and 1-indanone were purchased from Sigma-Aldrich and
used without further purification. The solvents dimethylformamide
(DMF), dichloromethane (DCM), ethanol, and 1,4-dioxane were of analytical
grade and were purchased from Sigma-Aldrich and used as received.
4,4′,4″-Benzene-1,3,5-triyl-tribenzoic acid (H₃btb) and requisite precursors were synthesized as described in the
literature.^{42 (link)} 5,5′,10,10′,15,15′-Hexamethyltruxene-2,7,12-tricarboxylic
acid (H₃hmtt) and requisite precursors were synthesized
as described in the literature.^{9 (link),11 (link)}