Tetraphenylporphyrin
- Formula: C44H30N4
- Molecular weight: 614.7358
- IUPAC Standard InChI: InChI=1S/C44H30N4/c1-5-13-29(14-6-1)41-33-21-23-35(45-33)42(30-15-7-2-8-16-30)37-25-27-39(47-37)44(32-19-11-4-12-20-32)40-28-26-38(48-40)43(31-17-9-3-10-18-31)36-24-22-34(41)46-36/h1-28,45,48H/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40-
- IUPAC Standard InChIKey: YNHJECZULSZAQK-LWQDQPMZSA-N
- CAS Registry Number: 917-23-7
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: 5,10,15,20-Tetraphenyl-21H,23H-porphyrin; meso-Tetraphenylporphine; meso-Tetraphenylporphyrine; Tetraphenyl porphine; α,β,γ,δ-Tetraphenylporphine; 21H,23H-Porphine, 5,10,15,20-tetraphenyl-; meso-Tetraphenylporphyrin; Porphine, 5,10,15,20-tetraphenyl-; 5,10,15,20-Tetraphenylporphine; 5,10,15,20-Tetraphenyl-21H,23H-porphine; NSC 18506; NSC 640184
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 621.3 ± 6.3 | kJ/mol | Ccb | Wu, Xu, et al., 1989 | see 62LI/LUO |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -22223.2 ± 6.3 | kJ/mol | Ccb | Wu, Xu, et al., 1989 | see 62LI/LUO |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔsubH° | 244.2 | kJ/mol | E | Wu, Xu, et al., 1989 | see 62LI/LUO; ALS |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 142. ± 3. | 626. to 707. | Fluoresc | Stefanov, Stibor, et al., 2004 | AC |
| 171. ± 2. | 550. | ME | Torres, Campos, et al., 2002 | Based on data from 543. to 555. K.; AC |
| 110.9 ± 5.0 | 603. | ME | Stephenson and Malanowski, 1987 | Based on data from 588. to 678. K. See also Bonderman, Cater, et al., 1970.; AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.69 ± 0.10 | IMRE | Chen, Pan, et al., 1991 | B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 6.3 ± 0.2 | LE | Nakato, Abe, et al., 1976 | LLK |
| 6.39 | PE | Khandelwal and Roebber, 1975 | Vertical value; LLK |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wu, Xu, et al., 1989
Wu, D.; Xu, G.; Qu, S.; Xue, R.; Gu, C.; Zhang, F.,
Standard enthalpies of combustion and formation of porphyrin derivatives,
Thermochim. Acta, 1989, 154, 233-245. [all data]
Stefanov, Stibor, et al., 2004
Stefanov, Andre; Stibor, Alexander; Dominguez-Clarimon, Alex; Arndt, Markus,
Sublimation enthalpy of dye molecules measured using fluorescence,
J. Chem. Phys., 2004, 121, 14, 6935, https://doi.org/10.1063/1.1792551
. [all data]
Torres, Campos, et al., 2002
Torres, Luis Alfonso; Campos, Myriam; Enriquez, Esteban; Patiño, Rodrigo,
The enthalpy of sublimation of 5,10,15,20-tetraphenylporphine and 5,10,15,20-tetrakis(4-methoxyphenyl)porphine,
The Journal of Chemical Thermodynamics, 2002, 34, 3, 293-302, https://doi.org/10.1006/jcht.2001.0920
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Bonderman, Cater, et al., 1970
Bonderman, Dean P.; Cater, E. David; Bennett, William Earl,
Vapor pressures, mass spectra, magnetic susceptibilities, and thermodynamics of some phthalocyanine compounds,
J. Chem. Eng. Data, 1970, 15, 3, 396-400, https://doi.org/10.1021/je60046a004
. [all data]
Chen, Pan, et al., 1991
Chen, H.L.; Pan, Y.H.; Groh, S.; Hagan, T.E.; Ridge, D.P.,
Gas-Phase Charge-Transfer Reactions and Electron Affinities of Macrocyclic, Anionic Nickel Complexes - Ni(SALEN), Ni(Tetraphenylporphyrin), and Derivatives.,
J. Am. Chem. Soc., 1991, 113, 7, 2766, https://doi.org/10.1021/ja00007a068
. [all data]
Nakato, Abe, et al., 1976
Nakato, Y.; Abe, K.; Tsubomura, H.,
Experimental determination of ionization potentials of tetraphenylporphine and metallotetraphenylporphines,
Chem. Phys. Lett., 1976, 39, 358. [all data]
Khandelwal and Roebber, 1975
Khandelwal, S.C.; Roebber, J.L.,
The photoelectron spectra of tetraphenylporphine and some metallotetraphenylporphyrins,
Chem. Phys. Lett., 1975, 34, 355. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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