Solvent Effects on the UV-Vis Absorption Properties and Tautomerisnn of N-Confused Tetraphenylporphyrin

被引：28

作者：

Aleman, Elvin A. ^{[3
]}

Joseph, Jojo ^{[1
,2
]}

Modarelli, David A. ^{[1
,2
]}

机构：

[1] Univ Akron, Ctr Laser & Opt Spect, Dept Chem, Akron, OH 44325 USA

[2] Univ Akron, Ctr Laser & Opt Spect, Knight Chem Lab, Akron, OH 44325 USA

[3] Calif State Univ Stanislaus, Dept Chem, Turlock, CA 95382 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 21期

基金：

美国国家科学基金会;

关键词：

ULTRAFAST DYNAMICS; ELECTRON-TRANSFER; RESONANCE RAMAN; CONDENSED-PHASE; PORPHYRINS; SPECTRA; SUBSTITUTION; MECHANISMS; ISOMER;

D O I：

10.1021/acs.joc.5b02244

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The two tautomeric forms of N-confused tetraphenylporphyrin (NCTPP) show distinctly different absorption spectra. The existence of each tautomer in solution has been shown to be strongly solvent-dependent. In the present work, we have studied the tautomerization using absorption spectroscopy in 15 different solvents. While changes in the two tautomers are not large in the Soret band region, the distinct spectral changes between the two tautomers in the Q-band region provide a convenient way to measure the concentration of each tautomer. The resulting data shows a strong correlation between the tautomer and the H-bond accepting ability of the solvent. The anomaly in this data is for the alcoholic solvents ethanol and methanol, for which we observe evidence for H-bonding, presumably between the exterior N2 nitrogen of the NCTPP and the O-H proton of the solvent.

引用

页码：11031 / 11038

页数：8

共 42 条

[11] The purple bacterial photosynthetic unit [J].

Cogdell, RJ ;

Fyfe, PK ;

Barrett, SJ ;

Prince, SM ;

Freer, AA ;

Isaacs, NW ;

McGlynn, P ;

Hunter, CN .

PHOTOSYNTHESIS RESEARCH, 1996, 48 (1-2) :55-63

[12] ASYMMETRICAL PORPHYRINS .1. SYNTHESIS, CHARACTERIZATION AND PHYSICOCHEMICAL PROPERTIES OF PHENYL/4-BENZYLOXYPHENYL 5,10,15,20-SUBSTITUTED PORPHYRINS [J].

DATTAGUPTA, N ;

MALAKAR, D ;

RICE, L ;

RIVERS, S .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (03) :629-632

[13] Synthesis of novel porphyrin-based biscalix[4]arenes [J].

Dudic, M ;

Lhoták, P ;

Král, V ;

Lang, K ;

Stibor, I .

TETRAHEDRON LETTERS, 1999, 40 (32) :5949-5952

[14] THE PRIMARY STEPS OF PHOTOSYNTHESIS [J].

FLEMING, GR ;

VANGRONDELLE, R .

PHYSICS TODAY, 1994, 47 (02) :48-55

[15] NH tautomerism of N-confused porphyrin [J].

Furuta, H ;

Ishizuka, T ;

Osuka, A ;

Dejima, H ;

Nakagawa, H ;

Ishikawa, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :6207-6208

[16] Confusion, inversion, and creation - a new spring from porphyrin chemistry [J].

Furuta, H ;

Maeda, H ;

Osuka, A .

CHEMICAL COMMUNICATIONS, 2002, (17) :1795-1804

[17] N-CONFUSED PORPHYRIN - A NEW ISOMER OF TETRAPHENYLPORPHYRIN [J].

FURUTA, H ;

ASANO, T ;

OGAWA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :767-768

[18] REFRACTIVE-INDEX EFFECTS ON THE ABSORPTION-SPECTRA OF MACROMOLECULES [J].

GARCIARUBIO, LH .

MACROMOLECULES, 1992, 25 (10) :2608-2613

[19] PHOTOPHYSICAL PROPERTIES OF CONFORMATIONALLY DISTORTED METAL-FREE PORPHYRINS - INVESTIGATION INTO THE DEACTIVATION MECHANISMS OF THE LOWEST EXCITED SINGLET-STATE [J].

GENTEMANN, S ;

MEDFORTH, CJ ;

FORSYTH, TP ;

NURCO, DJ ;

SMITH, KM ;

FAJER, J ;

HOLTEN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7363-7368

[20] Time line of discoveries: anoxygenic bacterial photosynthesis [J].

Gest, H ;

Blankenship, RE .

PHOTOSYNTHESIS RESEARCH, 2004, 80 (1-3) :59-70

← 1 2 3 4 5 →