Synthesis of low melting point porphyrins: A quest for new materials

References

• 1. Fetzer JC. In Large (C-24) Polycyclic Aromatic Hydrocarbons, Wiley: New York, 2000. Google Scholar
• 2. Janiak C. J. Chem. Soc. Dalton Trans. 2000; 3885–3896. Crossref, Google Scholar
• 3. Wrthner F. Chem. Commun. 2004; 1564–1579. Crossref, ISI, Google Scholar
• 4. (a) Sorokin AB. Chem. Rev. 2013; 113: 8152–8191. (b) Calvete MJF, Silva M, Pereira MM and Burrows HD. RSC Adv. 2013; 3: 22774–22789. (c) Mansuy D. C. R. Chim. 2007; 10: 392–413. (d) Cuesta-Aluja L, Castilla J, Masdeu-Bultó AM, Henriques CA, Calvete MJF and Pereira MM. J. Mol. Catal. A: Chem. 2016; in press DOI:. (e) Silva M, Azenha ME, Pereira MM, Burrows HD, Sarakha M, Forano C, Ribeiro MF and Fernandes A. Appl. Catal. B: Environ. 2010; 100: 1–9. (f) Rebelo SLH, Melo A, Coimbra R, Azenha ME, Pereira MM, Burrows HD and Sarakha M. Environ. Chem. Lett. 2007; 5: 29–33. Google Scholar
• 5. (a) Handbook of Porphyrin Science, Vol. 27, Ferreira GC, Kadish KM, Smith KM and Guilard R. (Eds.) World Scientific Publishers: Singapore, 2013; pp. 303–416. (b) Lovell JF, Liu TW, Chen J and Zheng G. Chem. Rev. 2010; 110: 2839–2857. (c) Dougherty TJ, Gomer CJ, Henderson BW, Jori G, Kessel D, Korbelik M, Moan J and Peng Q. J. Natl. Cancer Inst. 1998; 90: 889–905. (d) Vicente MGH. Curr. Med. Chem. 2001; 1: 175–194. (e) Ethirajan M, Chen Y, Joshi P and Pandey RK. Chem Soc Rev. 2011; 40: 340–362. (f) Calvete MJF, Simoes AVC, Henriques CA, Pinto SMA and Pereira MM. Curr. Org. Synth. 2014; 11: 127–140. (g) Pinto SMA, Tomé VA, Calvete MJF, Pereira MM, Burrows HD, Cardoso AMS, Castro MMCA, Tóth EM and Geraldes CFGC. J. Inorg. Biochem. 2016; 154: 50–59. (h) Simões AVC, Pinto SMA, Calvete MJF, Gomes CMF, Ferreira NC, Castelo-Branco M, Llop J, Pereira MM and Abrunhosa AJ, RSC Adv. 2015; 5: 99540–99546. (i) Vinagreiro CS, Goncalves NPF, Calvete MJF, Schaberle FA, Arnaut LG and Pereira MM. J. Fluorine Chem. 2015; 180: 161–167. (j) Arnaut LG, Pereira MM, Dabrowski JM, Silva EFF, Schaberle FA, Abreu AR, Rocha LB, Barsan MM, Urbanska K, Stochel G and Brett CMA. Chem. Eur. J. 2014; 20: 5346–5357. (k) Goncalves NPF, Simoes AVC, Abreu AR, Abrunhosa AJ, Dabrowski JM and Pereira MM. J. Porphyrins Phthalocyanines 2015; 19: 946–955. (l) Monteiro CJP, Pereira MM, Goncalves NPF, Carvalho CG, Neves ACB, Abreu AR, Arnaut LG and Silva AMS. J. Porphyrins Phthalocyanines 2012; 16: 316–323. (m) Pereira MM, Monteiro CJP, Simoes AVC, Pinto SMA, Arnaut LG, Sa GFF, Silva EFF, Rocha LB, Simoes S and Formosinho SJ. J. Porphyrins Phthalocyanines 2009; 13: 567–573. (n) Pereira MM, Arnaut LG, Formosinho SJ, Monteiro CJP., WO Patent 053707, 2006. (o) Pereira MM, Abreu AR, Goncalves NPF, Calvete MJF, Simoes AVC, Monteiro CJP, Arnaut LG, Eusebio ME and Canotilho J. Green Chem. 2012; 14: 1666–1672. Google Scholar
• 6. Simoes AVC, Adamowicz A, Dabrowski JM, Calvete MJF, Abreu AR, Stochel G, Arnaut LG and Pereira MM. Tetrahedron 2012; 68: 8767–8772. Crossref, ISI, Google Scholar
• 7. (a) Li LL and Diau EWG. Chem. Soc. Rev. 2013; 42: 291–304. (b) Chou J-H, Kosal ME, Nalwa HS, Rakow NA and Suslick KS. In The Porphyrin Handbook, Vol. 6, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: New York, 2000; pp. 43–131. (c) Walter MG, Rudine AB and Wamser CC. J. Porphyrins Phthalocyanines 2010; 14: 759–792. d) Calvete MJF, Int. Rev. Phys. Chem. 2012; 31: 319–366. (e) Pereira AMVM, Soares ARM, Calvete MJF and De la Torre G. J. Porphyrins Phthalocyanines 2009; 13: 419–428. (f) Pinto SMA, Lourenco MAO, Calvete MJF, Abreu AR, Rosado MTS, Burrows HD and Pereira MM. Inorg. Chem. 2012; 50: 7916–7918. (g) Marques AT, Pinto SMA, Monteiro CJP, de Melo JSS, Burrows HD, Scherf U, Calvete MJF and Pereira MM. J. Polym. Sci. A1. 2012; 50: 1408–1417. (h) Pinto SMA, Neves ACB, Calvete MJF, Abreu AR, Rosado MTS, Costa T, Burrows HD and Pereira MM. J. Photochem. Photobiol. A. 2012; 242: 59–66. (i) Henriques CA, Goncalves NPF, Abreu AR, Calvete MJF and Pereira MM. J. Porphyrins Phthalocyanines 2011; 15: 1–7. (j) Dini D, Meneghetti M, Calvete MJF, Arndt T, Liddiard C and Hanack M. Chem. Eur. J. 2010; 16: 1212–1220. (k) Dini D, Calvete M, Vagin S, Hanack M, Eriksson A and Lopes C. J. Porphyrins Phthalocyanines 2006; 10: 1165–1171. (l) Calvete MJF, Dini D, Hanack M, Sancho-Garcia JC, Chen WZ and Ji W. J. Mol. Model. 2006; 12: 543–550. (m) Dini D, Calvete MJF, Hanack M, Chen WZ and Ji W. Arkivoc 2006; 3: 77–96. (n) Li Y, Dini D, Calvete MJF, Hanack M and Sun W. J. Phys. Chem. A 2008; 112: 472–480. (o) Carvalho EFA, Calvete MJF, Cavaleiro JAS, Dini D, Meneghetti M and Tomé AC. Inorg. Chim. Acta 2010; 363: 3945–3950. Google Scholar
• 8. (a) de la Torre G, Vaquez P, Agullo-Lopez F and Torres T. Chem. Rev. 2004; 104: 3723–3750. (b) de la Torre G, Claessens CG and Torres T. Chem. Commun. 2007; 2000–2015. (c) de la Torre G, Vazquez P, Agullo-Lopez F and Torres T. J. Mater. Chem. 1998; 8: 1671–1683. (d) Bottari G, de la Torre G, Guldi DM and Torres T. Chem. Rev. 2010; 110: 6768–6816. (e) Claessens CG, Gonzalez-Rodriguez D and Torres T. Chem. Rev. 2002; 102: 835–853. (f) Cid JJ, Yum JH, Jang SR, Nazeeruddin MK, Ferrero EM, Palomares E, Ko J, Gratzel M and Torres T. Angew. Chem. Int. Edit. 2007; 46: 8358–8362. (g) Martinez-Diaz MV, de la Torrea G and Torres T. Chem. Commun. 2010; 46: 7090–7108. (h) Lee H, Leventis HC, Moon SJ, Chen P, Ito S, Haque SA, Torres T, Nuesch F, Geiger T, Zakeeruddin SM, Grätzel M and Nazeeruddin MK. Adv. Funct. Mater. 2009; 19: 2735–2742. (i) Hardin BE, Hoke ET, Armstrong PB, Yum JH, Comte P, Torres T, Frechet JMJ, Nazeeruddin MK, Gratzel M and McGehee MD. Nat. Photonics 2009; 3: 406–411. (j) O’Regan BC, Lopez-Duarte I, Martinez-Diaz MV, Forneli A, Albero J, Morandeira A, Palomares E, Torres T and Durrant JR. J. Am. Chem. Soc. 2008; 130: 2906–2907. (k) Claessens CG, Hahn U and Torres T. Chem. Rec. 2008; 8: 75–97. (l) O’Flaherty SM, Hold SV, Cook MJ, Torres T, Chen Y, Hanack M and Blau W. J. Adv. Mater. 2003; 15: 19–32. (m) Torres T. Angew. Chem. Int. Edit. 2006; 45: 2834–2837. (n) Rio Y, Rodriguez-Morgade MS and Torres T. Org. Biomol. Chem., 2008; 6: 1877–1894. (o) Sessler JL, Jayawickramarajah J, Gouloumis A, Torres T, Guldi DM, Maldonado S and Stevenson KJ. Chem. Commun. 2005; 1892–1894. (p) De la Torre G, Martinez-Diaz MV and Torres T. J. Porphyrins Phthalocyanines 1999; 3: 560–568. (q) Bottari G, Diaz DD and Torres T. J. Porphyrins Phthalocyanines 2006; 10: 1083–1100. (r) de la Torre G and Torres T. J. Porphyrins Phthalocyanines 2002; 6: 274–284. (s) Del Rey B, Martinez-Diaz MV, Barbera J and Torres T. J. Porphyrins Phthalocyanines 2000; 4: 569–573. (t) Silvestri F, Garcia-Iglesias M, Yum JH, Vazquez P, Martinez-Diaz MV, Gratzel M, Nazeeruddin MK and Torres T. J. Porphyrins Phthalocyanines 2009; 13: 369–375. Google Scholar
• 9. (a) Handbook of Porphyrin Science, Vol. 1–35, Kadish KM, Smith KM and Guilard R. (Eds.) World Scientific Publishers: Singapore, 2012–2014. (b) Vicente MGH and Smith KM. Curr. Org. Synth. 2014; 11: 3–28. (c) Pereira MM, Monteiro CJP and Peixoto AF. In Targets in Heterocyclic Systems: Chemistry and Properties, Vol. 12, Attanasi OA and Spinelli D. (Eds.) Italian Society of Chemistry: 2009; pp. 258–278. (d) Mamardashvili GM, Mamardashvili NZ and Berezin BD. Molecules 2000; 5: 762–766. (e) Lukyanets EA and Nemykin VN. J. Porphyrins Phthalocyanines 2010; 14: 1–40. (f) Dumoulin F, Durmus M, Ahsen V and Nyokong T. Coord. Chem. Rev. 2010; 254: 2792–2847. (g) Hanack M, Crucius G, Calvete MJF and Ziegler T. Curr. Org. Synth. 2014; 11: 59–66. (h) Carvalho EFA, Calvete MJF, Tomé AC and Cavaleiro JAS. Tetrahedron Lett. 2009; 50: 6882–6885. (i) Álvarez-Micó X, Calvete MJF, Hanack M and Ziegler T. Synthesis 2007; 14: 2186–2192. (j) Álvarez-Micó X, Calvete MJF, Hanack M and Ziegler T. Carbohyd. Res. 2007; 342: 440–447. Google Scholar
• 10. (a) Goodby JW, Robinson PS, Teo B-K and Cladis PE. Mol. Cryst. Liq. Cryst. 1980; 56: 303–309. (b) Gregg BA, Fox MA and Bard AJ. J. Chem. Soc., Chem. Commun. 1987; 1134–1135. (c) Ramasseul P, Maldivi P, Marchon J-C, Taylor M and Guillon D. Liq. Cryst. 1993; 13: 729–733. (d) Bruce DW and Wang QW. J. Chem. Soc. Chem. Commun. 1994; 18: 2089–2090. (e) Lee K-S, Shin J-I, Shim Y-S, Shim YK and Jin J-I. Bull. Korean Chem. Soc. 1994; 15: 817–818. (f) Ohta K, Yamaguchi N and Yamamoto I. J. Mater. Chem. 1998; 8: 2637–2680. (g) Ohta K, Ando N and Yamamoto I. Liq. Cryst. 1999; 26: 663–668. (h) Miwa H, Kobayashi N, Ban K and Ohta K. Bull. Chem. Soc. Jpn. 1999; 72: 2719–2728. (i) Eichhorn H. J. Porphyrins Phthalocyanines 2000; 4: 88–102. (j) Kimura M, Saito Y, Ohta K, Hanabusa K, Shirai H and Kobayashi N. J. Am. Chem. Soc. 2002; 124: 5274–5275. (k) Zhao Z and Liu G. Liq. Cryst. 2002; 29: 1335–1337. (l) Qi MH and Liu GF. J. Mater. Chem. 2003; 13: 2479–2484. (m) Segade A, Lupez-Calahorra F and Velasco D. Mol. Cryst. Liq. Cryst. 2005; 439: 201–208. (n) Yu M, Liu GF, Cheng YC and Xu WQ. Liq. Cryst. 2005; 32: 771–780. (o) Arunkumar C, Bhyrappa P and Varghese B. Tetrahedron Lett. 2006; 47: 8033–8037. (p) Michinobu T, Nakanishi T, Hill JP, Funahashi M and Ariga K. J. Am. Chem. Soc. 2006; 128: 10384–10385. (q) Stepien M, Donnio B and Sessler JL. Chem. Eur. J. 2007; 13: 6853–6863. (r) Babu SS, Aimi J, Ozawa H, Shirahata N, Saeki A, Seki S, Ajayaghosh A, Mchwald H and Nakanishi T. Angew. Chem. Int. Edit. 2012; 51: 3391–3395; Angew. Chem. 2012; 124: 3447–3451. (s) Wilson CJ, Wilson DA, Boyle RW and Mehl GH. J. Mater. Chem. C 2013; 1: 144–150. (t) Li H, Choi J and Nakanishi T. Langmuir 2013; 29: 5394–5406. (u) Hollamby MJ and Nakanishi T. J. Mater. Chem. C 2013; 1: 6178–6183. (v) Zielinska A, Leonowicz M, Li H and Nakanishi T. Curr. Opin. Coll. Interface Sci. 2014; 19: 131–139. (w) Jin Y-J, Bae J-E, Cho K-S, Lee W-E, Hwang D-Y and Kwak G, Adv. Funct. Mater. 2014; 24: 1928–1937. (x) Lewandowska U, Zajaczkowski W, Chen L, BouilliAre F, Wang D, Koynov K, Pisula W, Millen K and Wennemers H. Angew. Chem. Int. Edit. 2014; 53: 12537–12541; Angew. Chem. 2014; 126: 12745–12749. (y) Wu B, Chen K, Deng Y, Chen J, Liu D, Cheng R and Chen D. Chem. Eur. J. 2015; 21: 3671–3681. (z) Salamonczyk M, Pociecha D, Nowak-Krul A, Koszelewski D, Gryko DT and Gurecka E. Chem. Eur. J. 2015; 21: 7384–7388. Google Scholar
• 11. Shearman GC, Yahioglu G, Kirstein J, Milgrom LR and Seddon JM. J. Mater. Chem. 2009; 19: 598–604. Crossref, Google Scholar
• 12. Gregg BA, Fox MA and Bard AJ. J. Am. Chem. Soc. 1989; 111: 3024–3029. Crossref, ISI, Google Scholar
• 13. Nakai T, Ban K, Ohta K and Kimura M. J. Mater. Chem. 2002; 12: 844–850. Crossref, Google Scholar
• 14. Nowak-Król A, Gryko D and Gryko DT. Chem. Asian J. 2010; 5: 904–909. Crossref, ISI, Google Scholar
• 15. Henriques CA, Pinto SMA, Pineiro M, Canotilho J, Eusébio MES, Pereira MM and Calvete MJF. RSC Adv. 2015; 5: 64902–64910. Crossref, ISI, Google Scholar
• 16. Burrows HD, Rocha Gonsalves AM, Leitão MLP, Miguel MG and Pereira MM. Supramol. Sci. 1997; 4: 241–246. Crossref, Google Scholar
• 17. Henriques CA, Gonçalves NPF, Abreu AR, Calvete MJF and Pereira MM. J. Porphyrins Phthalocyanines 2012; 16: 290–296. Link, ISI, Google Scholar
• 18. Paliteiro C and Sobral A. Electrochimica Acta 2005; 50: 2445–2451. Crossref, ISI, Google Scholar
• 19. Cheng DO and Legoff E. Tetrahedron Lett. 1977; 18: 1469–1472. Crossref, Google Scholar
• 20. Koszelewski D, Nowak-Król A, Drobizhev M, Wilson CJ, Haley JE, Cooper TM, Romiszewski J, Górecka E, Anderson HL, Rebane A and Gryko DT. J. Mater. Chem. C 2013; 1: 2044–2053. Crossref, Google Scholar
• 21. Senge MO. Chem. Commun. 2011; 47: 1943–1960. Crossref, ISI, Google Scholar
• 22. Henriques CA, Pinto SMA, Aquino GLB, Pineiro M, Calvete MJF and Pereira MM. ChemSusChem 2014; 7: 2821–2824. Crossref, ISI, Google Scholar
• 23. Gonsalves AMAR, Varejao JMTB and Pereira MM. J. Heterocycl. Chem. 1991; 28: 635–640. Crossref, ISI, Google Scholar
• 24. Johnstone RAW, Nunes MLPG, Pereira MM, Gonsalves AMDR and Serra AC. Heterocycles 1996; 43: 1423–1437. Crossref, ISI, Google Scholar
• 25. Silva M, Fernandes A, Bebiano S, Calvete MJF, Ribeiro MF, Burrows HD and Pereira MM. Chem. Commun. 2014; 50: 6571–6573. Crossref, ISI, Google Scholar
• 26. Gatta GD, Richardson MJ, Sarge SM and Stolen S. Pure Appl. Chem. 2006; 78: 1455. Crossref, ISI, Google Scholar
• 27. Sabbah R, An XW, Chickos JS, Leitao MLP, Roux MV and Torres LA. Thermochim. Acta 1999; 331: 93. Crossref, ISI, Google Scholar
• 28. Experimental set-up for infrared and thermogravimetry measurements:Infrared spectra were obtained directly by reflectance on a spectrophotometer model FTIR Nicolet iS10 (Thermo Scientific), within the 4,000–600 cm${}^{-1}$ range, using an attenuated total reflection (ATR) accessory with a germanium crystal as holder. Simultaneous thermogravimetry (TG)–differential scanning calorimetry (DSC) curves were obtained with thermal analysis system, model TGA/DSC 1 Stare System (Mettler Toledo). The purge gas was an air flow of 50 mL min${}^{-1}$. A heating rate of 10${}^{\circ }$ C.min${}^{-1}$was adopted, with samples weighing about 5 mg. Alumina crucible was used for TG–DSC curves. Power compensation DSC was carried out with Perkin-Elmer Pyris 1 instrument using dry nitrogen, N50, at a flow rate 20 mL/min for purging gas. Aluminum pans 30 $\mu$l hermetically sealed were prepared for the sample (masses between 1.70 mg and 2.92 mg) and for the reference. Temperature calibration and apparatus was performed with biphenyl (CRM, LGC 2610, X >99.9%), Tfus $=$ 68.93${}^{\circ }$ C and indium (Perkin-Elmer, $\chi =$ 99.9%), Tfus $=$ 156.6${}^{\circ }$ C. The indium was used in the enthalpy calibrations ($\mathrm{\Delta }$fusH $=$ (3286 ± 13) J.mol${}^{-1})$. These values are in very good agreement with those reported in the literature (Refs. 26 and 27). The hot stage/DSC video microscopy study was carried out using a Linkam DSC600 system. The optical equipment attached to the hot stage system consists of a DMRB Leica microscope fitted with polarized light facilities to which a Sony CCD-IRIS/RGB video camera is attached. A Linkam system software with Real Time Video Measurement was used for image analysis. A small amount of the sample to be studied was placed in a glass crucible used as a cell, which was covered with a glass lid. Thermal cycles were followed by 200 × magnification and the images obtained by combined use of polarized light and wave compensators. The thermal program for the microscope examination was run at 10${}^{\circ }$ C.min${}^{-1}$. Google Scholar
• 29. Snyder RG and Schachtschneider JH. Spectrochim. Acta 1963; 19: 85–116. Crossref, ISI, Google Scholar
• 30. Snyder RG, Strauss HL and Elliger CA. J. Phys. Chem. 1982; 86: 5145. Crossref, ISI, Google Scholar
• 31. Yamashita M, Hirao A and Katoa M. J. Chem. Phys. 2011; 134: 144503. Crossref, ISI, Google Scholar
• 32. Chapman D. Chem. Rev. 1962; 62: 433. Crossref, ISI, Google Scholar
• 33. Yoshida H, Ichimura Y, Kinoshita R and Teramoto Y. Thermochim. Acta 1996; 282–283: 443. Crossref, ISI, Google Scholar