ArticlesNo Access
Synthesis, structure and physicochemical properties of a saddle-distorted porphyrin with a peripheral carboxyl group
Abstract
A saddle-distorted porphyrin bearing a carboxyl group as a hydrogen-bonding site on a meso-phenyl group was synthesized and characterized. A supramolecular structure with intermolecular hydrogen bonding was revealed by X-ray diffraction analysis. The effects of the peripheral carboxyl group on the physicochemical properties of the porphyrin as well as on self-assembly were investigated by spectroscopic measurements in solutions. The redox properties of the porphyrin and its Zn(II) complex were also studied by electrochemical measurements and their application to dye-sensitized solar cells was examined.
Dedicated to Professor John A. Shelnutt on the occasion of his 65th birthday
References
- a) Wasielewski MR. Chem. Rev. 1992; 92: 435–461. b) Medforth CJ, Wang Z, Martin KE, Song Y, Jacobsen JL and Shelnutt JA. Chem. Commun. 2009; 7261–7277. c) Wasielewski MR. Acc. Chem. Res. 2009; 42: 1910–1921 . Google Scholar
- a) Martinez-Diaz MM, Torre GDL and Torres T. Chem. Commun. 2010; 46: 7090–7108. b) Odobel F, Pleux LL, Pellegrin Y and Blart E. Acc. Chem. Res. 2010; 43: 1063–1071. c) Gust D, Moore TA and Moore AL. Acc. Chem. Res. 2009; 42: 1890–1898. d) Drain CM, Varotto A and Radivojevic I. Chem. Rev. 2009; 109: 1630–1658 . Google Scholar
- a) Kim D, Heo J, Ham S, Yoo H, Lee CH, Yoon H, Ryu D, Kim D and Jang WD. Chem. Commun. 2011; 47: 2405–2407. b) Tsuda A, Nagamine Y, Watanabe R, Nagatani Y, Ishii N and Aida T. Nat. Chem. 2010; 2: 977–983. c) Ohkawa H, Takayama A, Nakajima S and Nishide H. Org. Lett. 2006; 8: 2225–2228. d) Goldberg I. Chem. Commun. 2005; 1243–1254. e) Yamaguchi T, Ishii N, Tashiro K and Aida T. J. Am. Chem. Soc. 2003; 125: 13934–13935. f) Bhyrappa P, Wilson SR and Suslick KS. J. Am. Chem. Soc. 1997; 119: 8492–8502 . Google Scholar
- a) Nobukuni H, Shimazaki Y, Tani F and Naruta Y. Angew. Chem., Int. Ed. 2007; 46: 8975–8978. b) Gao Y, Zhang X, Ma C, Li X and Jiang J. J. Am. Chem. Soc. 2008; 130: 17044–17052. c) Hunter CA and Sanders JKM. J. Am. Chem. Soc. 1990; 112: 5525–5534 . Google Scholar
- Chem. Commun. 1777 (2008), DOI: 10.1039/b719625c. Google Scholar
- a) Liu T and Schneider HJ. Angew. Chem., Int. Ed. 2002; 46: 1368–1370. b) Kano K, Fukuda K, Wakami H, Nishiyabu R and Pasternack RF. J. Am. Chem. Soc. 2000; 122: 7494–7502 . Google Scholar
- a) Medforth CJ, Senge MO, Smith KM, Sparks LD and Shelnutt JA. J. Am. Chem. Soc. 1992; 114: 9859–9869. b) Gentemann S, Medforth CJ, Forsyth TP, Nurco DJ, Smith KM, Fajer J and Holten D. J. Am. Chem. Soc. 1994; 116: 7363–7368. c) Nurco DJ, Medforth CJ, Forsyth TP, Olmstead MM and Smith KM. J. Am. Chem. Soc. 1996; 118: 10918–10919. d) Retsek JL, Medforth CJ, Nurco DJ, Gentemann S, Chirvony VS, Smith KM and Holten D. J. Phys. Chem. B> 2001; 105: 6396–6411. e) Retsek JL, Drain CM, Kirmaier C, Nurco DJ, Medforth CJ, Smith KM, Sazanovich IV, Chirvony VS, Fajer J and Holten D. J. Am. Chem. Soc. 2003; 125: 9787–9800 . Google Scholar
- a) Harada R, Matsuda Y, Okawa H and Kojima T. Angew. Chem., Int. Ed. 2004; 43: 1825–1828. b) Kojima T, Harada R, Nakanishi T, Kaneko K and Fukuzumi S. Chem. Mater. 2007; 19: 51–58. c) Yokoyama, A, Kojima T and Fukuzumi S. Dalton Trans. 2011: 40: 6445–6450 . Google Scholar
- a) Nakanishi T, Kojima T, Ohkubo K, Hasobe T, Nakayama K and Fukuzumi S. Chem. Mater. 2008; 21: 7492–7500. b) Kojima T, Nakanishi T, Harada R, Ohkubo K, Yamauchi S and Fukuzumi S. Chem. Eur. J. 2007; 13: 8714–8725. c) Harada R and Kojima T. Chem. Commun. 2005; 716–718 . Google Scholar
- J. Am. Chem. Soc. 131, 577 (2009), DOI: 10.1021/ja806261q. Crossref, ISI, Google Scholar
- Angew. Chem., Int. Ed. 47, 6712 (2008), DOI: 10.1002/anie.200802601. Crossref, ISI, Google Scholar
- J. Am. Chem. Soc. 132, 10155 (2010), DOI: 10.1021/ja103889f. Crossref, ISI, Google Scholar
- Bio. Med. Chem. 13, 2413 (2005), DOI: 10.1016/j.bmc.2005.01.045. Crossref, ISI, Google Scholar
- J. Phys. Chem. C 114, 14290 (2010), DOI: 10.1021/jp105116y. Crossref, ISI, Google Scholar
- Inorg. Chem. 30, 239 (1991), DOI: 10.1021/ic00002a018. Crossref, ISI, Google Scholar
- CrystalStructure, Crystal Structure Analysis Package, 3.7.0; Rigaku and Rigaku/MSC: The Woodlands, TX, 2000–2005 . Google Scholar
- Wakita K, Yadokari-XG, Software for Crystal Structure Analyses, 2001. Kabuto C, Akine S, Nemoto T and Kwon E. Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses. J. Cryst. Soc. Jpn. 2009; 51: 218 . Google Scholar
- Sheldrick GM. SIR 97 and SHELX 97, Program for Crystal Structures Refinement; University of Göttingen: Göttingen, Germany, 1997 . Google Scholar
- Acta Crystallogr. A46, 194 (1990). Google Scholar
- Electrochem. Commun. 5, 369 (2003), DOI: 10.1016/S1388-2481(03)00070-5. Crossref, ISI, Google Scholar
- Tetrahedron Lett. 31, 5583 (1990), DOI: 10.1016/S0040-4039(00)97902-4. Crossref, ISI, Google Scholar
- The UV-vis spectrum of the crystalline sample in THF also supported the assignment that the (HNEt3) [H2DPP(COO)] was protonated during the recrystallization. The spectra exhbited intense absorption around 715 nm and the Soret band (λmax = 492 nm) showed red shift by 24 nm compared to that of [H2DPP(COO)]- formed by adding excess amount of triethylamine and the spectroscopic observations corresponded to the specific features of diprotonated DPPs . Google Scholar
- One of the oxygen atoms of the carboxyl group without forming hydrogen bond in Fig. 2b was found to form hydrogen bonding with a severely disordered i-PrOH molecule of crystallization, which was eliminated by the Squeeze method . Google Scholar
- Absorption maxima of the Soret band in CH2Cl2: 468 nm for H2DPP, 491 nm for H4DPPCl2, and 465 nm ZnDPP . Google Scholar
- Emission maxima in CH2Cl2: 786 nm for H2DPP, 761 nm for H4DPPCl2, and 684 nm ZnDPP . Google Scholar
- Chem. Commun. 4994 (2009), DOI: 10.1039/b910077f. Google Scholar
- J. Am. Chem. Soc. 122, 7494 (2000), DOI: 10.1021/ja000738g. Crossref, ISI, Google Scholar
- In the previous report (see reference 11), we observed the 1H signals for 4-pyridine carboxylate in the (H4DPP)(4-pyridine carboxylate)2 supramolecule at 5.97 and 7.68 ppm for the 3,5- and 2,6-protons, respectively. The degree of the up-field shifts is similar to those observed in this work . Google Scholar
- a) Bessho T, Zakeeruddin SM, Yeh CY, Diau EWG and Grätzel M. Angew. Chem., Int. Ed. 2010; 49: 6646–6649. b) Lee, CW, Lu HP, Lan, CM, Huang, YL, Liang YR, Yen WN, Liu YC, Lin YS, Diau EWG and Yeh CY. Chem. Eur. J. 2009; 15: 1403–1412 . Google Scholar
Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 44 volumes (9 sets)
Handbook of Porphyrin Science now available in 44 volumes (9 sets)
