2,5-Diphenylfuran Singlet oxygen

Usui, Y.; Koike, H.; Kurimura, Y.
Bull. Chem. Soc. Jpn. 60, 3373-3378 (1987)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® 2,5-Diphenylfuran endoperoxide
Reference Reaction: DPBF + ¹O₂^* ®
Solvent: CH₃CN

k = 3.7 × 10⁸(L mol^-1 s^-1), b = 8.3 × 10^-5(mol L^-1), b_ref = 1.3 × 10^-5(mol L^-1), k_reference = 2.4 × 10⁹(L mol^-1 s^-1), T = 293K

Experimental method: Photolysis
Analytical method: chemical analysis
Data type: Relative value measured by steady state method

Photosensitizer = Methylene Blue; used solvent k_d = 3 × 10⁴ s^-1. [O₂] = air.

Clennan, E.L.; Mehrsheikh-Mohammadi, M.E.
J. Am. Chem. Soc. 106, 7112-7118 (1984)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: CH₂Cl₂

k = 7.0 × 10⁷(L mol^-1 s^-1)

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements using indicator

Photosensitizer = Mesoporphyrin IX, dimethyl ester; used solvent k_d = 1 × 10⁴ s^-1; Indicator = 1,3-Diphenylisobenzofuran.

Clennan, E.L.; Mehrsheikh-Mohammadi, M.E.
J. Am. Chem. Soc. 106, 7112-7118 (1984)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: CH₂Cl₂

k = 5.2 × 10⁷(L mol^-1 s^-1)

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Derived from steady state measurements using indicator

Photosensitizer = Indicator = Rubrene; used solvent k_d = 1 × 10⁴ s^-1; k for indicator = 3.3 × 10⁷ L/(mol·s).

Gorman, A.A.; Lovering, G.; Rodgers, M.A.J.
J. Am. Chem. Soc. 101, 3050-3055 (1979)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: C₆H₅CH₃

Enthalpy of activation = 0(kJ mol^-1), Entropy of activation = -100(J K^-1 mol^-1), Temperature range 223 to 353 K
k = 1.0 × 10⁸(L mol^-1 s^-1)

Experimental method: Pulse radiolysis
Analytical method: vis-UV absorption
Data type: Absolute value measured directly using indicator

Photosensitizer = Naphthalene; Indicator = 1,3-Diphenylisobenzofuran. [Sensitizer] = 10^-2 (mol L^-1).

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: 1-BuOH

k = 5.0 × 10⁷(L mol^-1 s^-1), b = 1.0 × 10^-3(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran; used solvent k_d = 5.2 × 10⁴ s^-1; Solvent contained 1% MeOH.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: tert-BuOH

k = 3.6 × 10⁷(L mol^-1 s^-1), b = 8.3 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran; used solvent k_d = 3.0 × 10⁴ s^-1; Solvent contained 1% MeOH.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: C₅H₅N

k = 6.1 × 10⁷(L mol^-1 s^-1), b = 9.9 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran; used solvent k_d = 6.0 × 10⁴ s^-1; Solvent contained 1% MeOH.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: c-C₆H₁₁OH

k = 5.3 × 10⁷(L mol^-1 s^-1), b = 1.2 × 10^-3(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran; used solvent k_d = 6.2 × 10⁴ s^-1; Solvent contained 1% MeOH.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: Methyl benzoate

k = 4.1 × 10⁷(L mol^-1 s^-1), b = 6.1 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran; used solvent k_d = 2.5 × 10⁴ s^-1; Solvent contained 1% MeOH.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: CH₂Cl₂

k = 5.1 × 10⁷(L mol^-1 s^-1), b = 1.4 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran. used solvent k_d = 7.1 × 10³ s^-1.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: CH₃CN

k = 1.4 × 10⁸(L mol^-1 s^-1), b = 1.3 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran. used solvent k_d = 1.8 × 10⁴ s^-1.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: Ethyl acetate

k = 3.0 × 10⁷(L mol^-1 s^-1), b = 6.9 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran. used solvent k_d = 2.1 × 10⁴ s^-1.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: (CH₃)₂CO

k = 1.4 × 10⁸(L mol^-1 s^-1), b = 1.7 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran. used solvent k_d = 2.4 × 10⁴ s^-1.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: CHCl₃

k = 2.2 × 10⁷(L mol^-1 s^-1), b = 2.0 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran. used solvent k_d = 4.4 × 10³ s^-1.

Porter, D.J.T.; Ingraham, L.L.
Biochim. Biophys. Acta 334, 97-102 (1974)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products
Solvent: D₂O

b = 7.7 × 10^-5(mol L^-1), T = 296K

Experimental method: Photolysis
Analytical method: vis-UV absorption
Data type: Relative value measured by steady state method

Photosensitizer = Methylene Blue; meas. k_d/k = 7.7 × 10^-5 mol/L rel. to k_d/k = 4.6 × 10^-4 mol/L in H₂O.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: MeOH

k = 1.0 × 10⁸(L mol^-1 s^-1), b = 8.8 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran. used solvent k_d = 9.0 × 10⁴ s^-1.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: 2-PrOH

k = 4.8 × 10⁷(L mol^-1 s^-1), b = 1.0 × 10^-3(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Methylene Blue; Indicator = 1,3-Diphenylisobenzofuran; used solvent k_d = 5.0 × 10⁴ s^-1; Solvent contained 1% MeOH.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: THF

k = 7.5 × 10⁷(L mol^-1 s^-1), b = 5.9 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Rose Bengal dianion; used solvent k_d = 4.3 × 10⁴ s^-1; Indicator = 1,3-Diphenylisobenzofuran.

Brewer, D.R.,III
Ph.D., Thesis, Georgetown Univ., Wash. D.C., 1974, 694p.

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: Dioxane

k = 2.7 × 10⁷(L mol^-1 s^-1), b = 1.1 × 10^-3(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Rose Bengal dianion; used solvent k_d = 2.9 × 10⁴ s^-1; Indicator = 1,3-Diphenylisobenzofuran.

Young, R.H.; Brewer, D.; Keller, R.A.
J. Am. Chem. Soc. 95, 375-379 (1973)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: MeOH

k = 4.6 × 10⁷(L mol^-1 s^-1)

Experimental method: Flash photolysis
Analytical method: vis-UV absorption
Data type: Absolute value measured directly using indicator
Excitation wavelength: 583 nm

Photosensitizer = Rose Bengal dianion; Indicator = 1,3-Diphenylisobenzofuran.

Olmsted, J.,III; Akashah, T.
J. Am. Chem. Soc. 95, 6211-6215 (1973)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products
Solvent: MeOH

k_react ~ 5 × 10⁵(L mol^-1 s^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements

Photosensitizer = Rose Bengal dianion; used solvent k_d = 1.4 × 10⁵ s^-1; used quantum yield for sensitizer = 0.76.

Young, R.H.; Wehrly, K.; Martin, R.L.
J. Am. Chem. Soc. 93, 5774-5779 (1971)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products
Solvent: H₂O

b = 4.6 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Relative value measured by steady state method

Photosensitizer = Rose Bengal dianion; meas. k_d/k = 4.6 × 10^-4 mol/L rel. to k_d/k = 9.5 × 10^-4 mol/L in MeOH.

Young, R.H.; Wehrly, K.; Martin, R.L.
J. Am. Chem. Soc. 93, 5774-5779 (1971)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products
Solvent: Ethylene glycol

b = 3.5 × 10^-4(mol L^-1)

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Relative value measured by steady state method

Photosensitizer = Rose Bengal dianion; meas. k_d/k = 3.5 × 10^-4 mol/L rel. to k_d/k = 9.5 × 10^-4 mol/L in MeOH.

Young, R.H.; Wehrly, K.; Martin, R.L.
J. Am. Chem. Soc. 93, 5774-5779 (1971)

Reaction: 2,5-Diphenylfuran + ¹O₂^* ® products and/or physical quenching
Solvent: MeOH

b = 9.5 × 10^-4(mol L^-1), T = 298K

Experimental method: Photolysis
Analytical method: vis-UV emission
Data type: Derived from steady state measurements using indicator

Photosensitizer = Rose Bengal dianion; Indicator = 1,3-Diphenylisobenzofuran; meas. k_d/k = 9.5 × 10^-4 mol/L. Also reported rel. k_d/k for MeOH/H₂O (12:88, 40:60, 66:34, 81:19) and MeOH/Ethylene glycol (75:25, 50:50, 25:75).