LI Chen, LI Jian-feng, DUAN Wu-biao etc. Synthesis, Spectral and Electrochemical Properties of A New Tailed Porphyrin[J]. Chinese Journal of Luminescence, 2016,37(2): 158-164
LI Chen, LI Jian-feng, DUAN Wu-biao etc. Synthesis, Spectral and Electrochemical Properties of A New Tailed Porphyrin[J]. Chinese Journal of Luminescence, 2016,37(2): 158-164 DOI: 10.3788/fgxb20163702.0158.
Synthesis, Spectral and Electrochemical Properties of A New Tailed Porphyrin
TPP-BzIm and different transition metalloporphyrins (Fe
Co
Zn) were synthesized and characterized by
1
H NMR
MS
IR
UV-Vis. The spectral and electrochemical properties were studied by UV-Vis spectrum
fluorescence spectrum and cyclic voltammetry method. Compared with tetraphenyporphyrin(H
2
TPP)
the absorption and emission peaks of the tailed porphyrin have obvious red-shifts. The CV curves of Fe
Co metalloporphyrins indicate that Fe and Co undergo the changing of oxidation state in addition to the redox on the porphyrin ring.
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references
XIE Y S, TANG Y Y, WU W J, et al.. Porphyrin cosensitization for a photovoltaic efficiency of 11.5%: a record for non-ruthenium solar cells based on iodine electrolyte [J]. J. Am. Chem. Soc., 2015, 137(44):14055-14058.
DING Y B, TANG Y Y, ZHU W H, et al.. Fluorescent and colorimetric ion probes based on conjugated oligopyrroles [J]. Chem. Soc. Rev., 2015, 44(5):1101-1112.
WANG Y Q, CHEN B, WU W J, et al.. Efficient solar cells sensitized by porphyrins with an extended conjugation framework and a carbazole donor: from molecular design to cosensitization [J]. Angew. Chem. Int. Ed., 2014, 53(40):10779-10783.
MALIGASPE E, KUMPULAINEN T, SUBBAIYAN N K, et al.. Electronic energy harvesting multi BODIPY-zinc porphyrin dyads accommodating fullerene as photosynthetic composite of antenna-reaction center [J]. Phys. Chem. Chem. Phys., 2010, 12(27):7434-7444.
MANSUY D. Biomimetic catalysts for selective oxidation in organic chemistry [J]. Pure Appl. Chem., 1990, 62(4):741-746.
MOGHADAM M, TANGESTANINEJAD S, MIRKHANI V, et al.. High-valent tin (Ⅳ) porphyrin, SnⅣ (TPP) (BF4)2, as an efficient catalyst for the ring-opening of epoxides [J]. Catal. Commun., 2007, 8(12):2087-2095.
HE L, CHAN P W H, TSUI W M, et al.. Ruthenium (Ⅱ) porphyrin-catalyzed amidation of aromatic heterocycles [J]. Org. Lett., 2004, 6(14):2405-2408.
ALVARO M, ATIENZAR P, DE LA CRUZ P, et al.. Synthesis, photochemistry, and electrochemistry of single-wall carbon nanotubes with pendent pyridyl groups and of their metal complexes with zinc porphyrin. Comparison with pyridyl-bearing fullerenes [J]. J. Am. Chem. Soc., 2006, 128(20):6626-6635.
COLLMAN J P, BRAUMAN J I, DOXSEE K M, et al.. Synthesis and characterization of 'tailed picket fenceporphyrins [J]. J. Am. Chem. Soc., 1980, 102(12):4182-4192.
YOUNG R, CHANG C K. Synthesis and characterization of blocked and ligand-appended hemes derived from atropisomeric meso-diphenylporphyrins [J]. J. Am. Chem. Soc., 1985, 107(4):898-909.
BERTO T C, PRANEETH V K K, GOODRICH L E, et al.. Iron-porphyrin NO complexes with covalently attached N-donor ligands: formation of a stable six-coordinate species in solution [J]. J. Am. Chem. Soc., 2009, 131(47):17116-17126.
郭灿城,尹振明,朱锦涛,等. 一种新型红色荧光卟啉的合成、表征及光谱性质 [J]. 高等学校化学学报, 2002, 23(5):832-834. GUO C C, YIN Z M, ZHU J T, et al.. Synthesis, characterization and spectrum property of a new red-fluorescence porphine [J]. Chem. J. Chin. Univ., 2002, 23(5):832-834. (in Chinese)
朱志昂,张智慧,江冬青,等. 四苯基卟吩及取代四苯基卟啉-铁配合物的紫外可见光谱研究 [J]. 光谱学与光谱分析, 1990, 10(1):15-20. ZHU Z A, ZHANG Z H, JIANG D Q, et al.. UV-Vis spectra of ms-tetraphenylporphin and para-substiruted tetraphenylporphin-yrin complexes of chloro-iron(Ⅲ) [J]. Spectrosc. Spectral Anal., 1990, 10(1):15-20. (in Chinese)
左国防,雷新有,杜捷,等. 系列卟啉化合物的合成及其光谱和电化学性质研究 [J]. 光谱实验室, 2008, 25(3):290-296. ZUO G F, LEI X Y, DU J, et al.. Study on synthesis and spectral and electrochemical properties of a series of porphyrins [J]. Chin. J. Spectrosc. Laborat., 2008, 25(3):290-296. (in Chinese)
单凝,王彬彬,连文慧,等. 稀土金属尾式组氨酸卟啉配合物的合成及光电性质 [J]. 高等学校化学学报, 2011, 33(18):1651-1656. SHAN N, WANG B B, LIAN W H, et al.. Synthesis and surface photovoltage property of tailed histidine-linked lanthanon metalloporphyrins [J]. Chem. J. Chin. Univ., 2011, 33(18):1651-1656. (in Chinese)
肖竦. 四苯基卟啉及其衍生物的光谱性质研究 [D]. 武汉: 华中师范大学, 2000. XIAO S. Studies on Spectral Properties of Tetraphenylporphine and Its Substitutive Derivatives [D]. Wuhan: Central China Normal University, 2000. (in Chinese)
夏梅君,申琦,郭九吉,等. 取代四苯基卟啉的紫外、荧光光谱及电化学性质 [J]. 郑州大学学报(理学版), 2010, 42(4):83-87. XIA M J, SHEN Q, GUO J J, et al.. The UV-Vis, fluorescence and electrochemical properties of tetraphenylporphyrin and its derivatives [J]. J. Zhengzhou Univ.(Nat. Sci. Ed.), 2010, 42(4):83-87. (in Chinese)
MIZUTANI T, EMA T, YOSHIDA T, et al.. Recognition of -amino acid esters by zinc porphyrin derivatives via coordination and hydrogen bonding interactions. Evidence for two-point fixation from thermodynamic and induced circular dichroism spectroscopic studies [J]. Inorg. Chem., 1993, 32(10):2072-2077.
王树军,彭玉苓,刘光仙,等. 卟啉类化合物与人血清白蛋白相互作用的研究进展 [J]. 化学通报, 2013, 76(6):491-498. WANG S J, PENG Y L, LIU G X, et al.. Progress on the interaction between porphyrins and human serum albumin [J]. Chemistry, 2013, 76(6):491-498. (in Chinese)
SEYBOLD P G, GOUTERMA M. Porphyrins: XIII: fluorescence spectra and quantum yields [J]. J. Mol. Spectrosc., 1969, 31(1-13):1-13.
何亚楠,邰子厚,喻诚,等. 卟啉化合物电化学性质研究Ⅰ. 5, 10, 15, 20-四-(4-乙酰氧基苯)卟吩及其Cu、Zn、Fe、Co、Ni配合物的合成及循环伏安研究 [J]. 无机化学学报, 1993, 9(4):336-341. HE Y N, TAI Z H, YU C, et al.. Investigation of electrochemical characteristics of porphyrins. I. cyclic voltammetry investigation of 5, 10, 15, 20-tetrakis-(4-acetoxyphenyl) porphine and its Cu, Zn, Fe, Co, Ni complexes [J]. J. Inorg. Chem., 1993, 9(4):336-341. (in Chinese)
TRUXILLO L A, DAVIS D G. Electrochemistry of cobalt tetraphenylporphyrin in aprotic media [J]. Anal. Chem., 1975, 47(13):2260-2267.
KADISH K M, MORRISON M M. Substituent effects on the redox reactions of tetraphenylporphyrins [J]. Bioinorg. Chem., 1977, 7(2):107-115.