Anthracene

All chemicals were purchased from commercial sources and used without further purification. Citric acid was obtained from SD-Fine chemicals (SDFCL), L-tyrosine from Sisco Research laboratories (SRL. Pvt. Ltd), sodium hydroxide, and anthracene from MERCK chemicals. Solvents (spectroscopic grade) from Qualigens have been used for analysis. Deuterated dimethyl sulfoxide (DMSO-d₆) was obtained from Sigma-Aldrich chemicals and used to record ¹H NMR and ¹³C NMR spectra.

Anthracene, oleic acid, linoleic acid, acetonitrile, methylene blue (MB), DABCO, BHT, BHA, TBHQ, 2-nitrobenzaldehyde, 3-nitrobenzaldehyde, and 4-nitrobenzaldehyde were purchased from Merck or Sigma-Aldrich (Vienna, Austria) and Alfa Aesar (Karlsruhe, Germany) without further purification. 5,10,15,20-Tetrakis(tolyl)porphyrin (H₂TTP) and its ferric complex TTPFeCl were synthesized according to the literature [13 (link),14 (link)].

Compound 1 was prepared according to the reported procedure [6 (link)]. Anthracene (Merck, Darmstadt, Germany, 99.5%) was purchased and used without further purification.
UV/Vis spectra were recorded on a V-570 UV/VIS/NIR spectrophotometer (JASCO, Hachioji, Japan). Fluorescence spectra were obtained on an F-4500 fluorescence spectrophotometer (Hitachi, Tokyo, Japan). Fluorescence quantum yields were determined by using a C9920-02 absolute PL quantum yield measurement system (Hamamatsu Photonics, Hamamatsu, Japan).
All theoretical calculations were performed by using Gaussian 09 [45 ] and 16 [46 ] on a PRIMERGY RX300 system (Fujitsu, Tokyo, Japan) of the Research Center for Computational Science, Japan. The structures of the S₀ and S₁ states of 1 and Anthracene were optimized at the B3LYP/6-31G(d) and TD-DFT B3LYP/6-31G(d) levels, respectively, and the optimization was confirmed by frequency calculations. The results are summarized in Tables S1 and S2. Transition properties of 1 and Anthracene were calculated at the TD-DFT B3LYP/6-31G(d) level by using the optimized structures. The results are summarized in Tables S3 and S4.

Anthracene, acetic anhydride, aluminum chloride (AlCl₃), diethyl ether
(DEE), methanol (CH₃OH), phosphorous pentoxide, acetic acid
(CH₃COOH), sulfuric acid (H₂SO₄), magnesium
sulfate (MgSO₄), hydrochloric acid (HCl), sodium bicarbonate
(NaHCO₃), titanium tetrachloride (TiCl₄), calcium
hydride (CaH₂), benzophenone were purchased from Merck at the highest
purity available and used as received. Sodium (Na) metal was purchased from Alfa
Aesar and used as received. Isobutylene (IB) was purchased from Scott Specialty
Gases and was dried by passing through columns packed with anhydrous calcium
sulfate, cobalt chloride, moisture sensitive color indicator, silica gel and
condensed into a N₂ atmosphere reactor at −40 °C
prior to use.
Phenylmagnesium bromide (PhMgBr, 3M in DEE solution) was purchased from Sigma
Aldrich and used as received.
Dichloromethane (DCM), n-hexane, tetrahydrofuran (THF) and
2,6-di-tert-butylpyridine (DtBP) were purchased from Merck.
DCM and n-hexane were initially refluxed over calcium hydride;
followed by distillation in reduced pressure over sodium mirror and phosphorous
pentoxide, respectively. THF was distilled over sodium metal and benzophenone.
DtBP was purified by distillation over calcium hydride.

All manipulations have been performed under prepurified N₂ using standard Schlenk techniques. Dry solvents were dispensed from a solvent purification system (Innovative Technologies; Newburyport, MA, USA). Commercial reagents 4-bromo-naphthalic anhydride (Merck, Darmstadt, Germany, 95%), Ammonium hydroxide solution (A.C.S reagent, 28–30%), ethynyltrimethylsilane (Merck, 98%), Copper (I) iodide (Merck, 98%), triethylamine (Merck, 99.5%), 1,3,5-triaza-7-phosphaadamantane (Merck, 97%), tetrabutylammonium fluoride (TBAF, 1M in tetrahydrofuran, Panreac), naphthalene (Koch-Light Labs, Haverhill, UK), anthracene (≥99%, Merck), phenanthrene (≥99.5%, Merck), and pyrene (≥99%, Merck) were used as received.

Benzoate, 3-hydroxyBenzoate, 4-hydroxyBenzoate, cinnamate, 3-hydroxycinnamate, salicylate, nicotinate, anthranilate, 4-aminoBenzoate, 2-aminophenol, benzamide, simazine, tryptophan, and methyl viologen dichloride hydrate (paraquat, PQ) were obtained from Sigma-Aldrich (St. Louis, MO, United States). Benzene (>99.7% purity), toluene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, and 30% (w v^-1) hydrogen peroxide (H₂O₂) were purchased from Merck (Darmstadt, Germany).

Pure PAHs consist of naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, and chrysene purchased from Merck (Darmstadt, Germany). A stock standard solution of PAHs has been prepared at a concentration of 100 mg L^–1 in methanol. Acetonitrile and methanol with HPLC grade were from Carlo Erba (ValdeReuil, France). The HPLC-grade water and the other solvents and chemicals have been obtained from Merck (Darmstadt, Germany). The Alu wire was supplied from Simcat Co. in Tabriz (Iran) and employed as the SPME fiber substrate. Tomato, potato samples have been acquired from Seed and Plant Research Improvement Institute in Karaj (Iran). Sangak bread has been purchased from the Shahrenan-Jihot company (Karaj, Iran).