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Greener shades of blue: Green chemistry as an opportunity to improve the approach to the synthesis of phthalocyanines

Istituto di Struttura della Materia (ISM) Consiglio Nazionale delle Ricerche (CNR), Via Salaria km 29.300, 00015 Monterotondo, Italy

E-mail Address: gloria.zanotti@cnr.it

Correspondence to: Gloria Zanotti, Tel: +390690672318.

SPP full member in good standing.

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Laura Mancini

Istituto di Struttura della Materia (ISM) Consiglio Nazionale delle Ricerche (CNR), Via Salaria km 29.300, 00015 Monterotondo, Italy

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Anna Maria Paoletti

Istituto di Struttura della Materia (ISM) Consiglio Nazionale delle Ricerche (CNR), Via Salaria km 29.300, 00015 Monterotondo, Italy

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Giovanna Pennesi

Istituto di Struttura della Materia (ISM) Consiglio Nazionale delle Ricerche (CNR), Via Salaria km 29.300, 00015 Monterotondo, Italy

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, and

Venanzio Raglione

Istituto di Struttura della Materia (ISM) Consiglio Nazionale delle Ricerche (CNR), Via Salaria km 29.300, 00015 Monterotondo, Italy

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https://doi.org/10.1142/S1088424623500062Cited by:2 (Source: Crossref)

Abstract

Green chemistry has emerged as a powerful tool to rationally design environmentally sustainable chemical processes by choosing safe chemicals and minimizing the production of waste. This article focuses on the opportunity, yet underexplored, to evaluate the green syntheses of phthalocyanines by means of metrics such as the E-factor and EcoScale, in a view to better assess their sustainability and provide insights on their viability with respect to standard procedures.

Dedicated to Prof. Tomás Torres on the occasion of his 70^th birthday

Keywords:

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References

1. Anastas PT and Warner JC. Green Chemistry: Theory and Practice. Oxford University Press; 1998. Google Scholar
2. Gounden D, Nombona N and van Zyl WE. Coord. Chem. Rev. 2020; 420: 213359. Crossref, Web of Science, Google Scholar
3. Wang M, Zhang Z, Zhong H, Huang X, Li W, Hambsch M, Zhang P, Wang Z, St., Petkov P, Heine T, Mannsfeld SCB, Feng X and Dong R. Angew. Chem. Int. Ed. 2021; 60: 18666–18672. Web of Science, Google Scholar
4. Lo P-C, Rodríguez-Morgade MS, Pandey RK, Ng DKP, Torres T and Dumoulin F. Chem. Soc. Rev. 2020; 49: 1041–1056. Crossref, Web of Science, Google Scholar
5. Boutin E, Wang M, Lin JC, Mesnage M, Mendoza D, Lassalle-Kaiser B, Hahn C, Jaramillo TF and Robert M. Angew. Chem. Int. Ed. 2019; 58: 16172–16176. Crossref, Web of Science, Google Scholar
6. Wang M, Torbensen K, Salvatore D, Ren S, Joulié D, Dumoulin F, Mendoza D, Lassalle-Kaiser B, Işci U, Berlinguette CP and Robert M. Nat. Commun. 2019; 10: 3602. Crossref, Web of Science, Google Scholar
7. Boileau NT, Cranston R, Mirka B, Melville OA and Lessard BH. RSC Adv. 2019; 9: 21478–21485. Crossref, Web of Science, Google Scholar
8. Melville OA, Lessard BH and Bender TP. ACS Appl. Mater. Interfaces 2015; 7: 13105–13118. Crossref, Web of Science, Google Scholar
9. Ragoussi M-E, Yum J-H, Chandiran AK, Ince M, de la Torre G, Grätzel M, Nazeeruddin MK and Torres T. ChemPhysChem 2014; 15: 1033–1036. Crossref, Web of Science, Google Scholar
10. Cid J-J, Yum J-H, Jang S-R, Nazeeruddin MK, Martínez-Ferrero E, Palomares E, Ko J, Grätzel M and Torres T. Angew. Chem. Int. Ed. 2007; 46: 8358–8362. Crossref, Web of Science, Google Scholar
11. Ikeuchi T, Nomoto H, Masaki N, Griffith MJ, Mori S and Kimura M. Chem. Commun. 2014; 50: 1941–1943. Crossref, Web of Science, Google Scholar
12. Urbani M, de la Torre G, Nazeeruddin MK and Torres T. Chem. Soc. Rev. 2019; 48: 2738–2766. Crossref, Web of Science, Google Scholar
13. Wu S, Chen C, Liu Q, Peng T, Li R and Zhang J. ACS Appl. Energy Mater. 2018; 1: 5539–5547. Web of Science, Google Scholar
14. Yu Z, Hagfeldt A and Sun L. Coord. Chem. Rev. 2020; 406: 213143. Crossref, Web of Science, Google Scholar
15. Feng Y, Hu Q, Rezaee E, Li M, Xu Z, Lorenzoni A, Mercuri F and Muccini M. Adv. Energy Mater. 2019; 9: 1901019. Crossref, Web of Science, Google Scholar
16. Koyun Ö, Gördük S, Keskin B, Çetinkaya A, Koca A and Avcıata U. Polyhedron 2016; 113: 35–49. Crossref, Web of Science, Google Scholar
17. Shaabani A, Maleki-Moghaddam R, Maleki A and Rezayan AH. Dyes Pigments 2007; 74: 279–282. Crossref, Web of Science, Google Scholar
18. Gonzalez ACS, Damas L, Aroso RT, Tomé VA, Dias LD, Pina J, Carrilho RMB and Pereira MM. J. Porphyr. Phthalocyanines 2020; 24: 947–958. Link, Web of Science, Google Scholar
19. Youssef TE. Polyhedron 2010; 29: 1776–1783. Crossref, Web of Science, Google Scholar
20. Saito Y, Higuchi T, Sugimori H and Yabu H. ChemNanoMat 2015; 1: 92–95. Crossref, Web of Science, Google Scholar
21. Langerreiter D, Kostiainen MA, Kaabel S and Anaya-Plaza E. Angew. Chem. Int. Ed. 2022; 61: e202209033. Crossref, Web of Science, Google Scholar
22. Li D, Ge S, Sun G, He Q, Huang B, Tian G, Lu W, Li G, Chen Y, An S and Zheng Z. Dyes Pigments 2015; 113: 200–204. Crossref, Web of Science, Google Scholar
23. Li D, Ge S, Yuan T, Gong J, Huang B, Tie W and He W. CrystEngComm 2018; 20: 2749–2758. Crossref, Web of Science, Google Scholar
24. Yadav KK, Poonam and Chauhan SMS. Synth. Commun. 2014; 44: 2797–2807. Crossref, Web of Science, Google Scholar
25. Lo P-C, Cheng DYY and Ng DKP. Synthesis 2005; 7: 1141–1147. Google Scholar
26. Shaabani A, Hooshmand SE, Afshari R, Shaabani S, Ghasemi V, Atharnezhad M and Akbari M. J. Solid State Chem. 2018; 258: 536–542. Crossref, Web of Science, Google Scholar
27. Zanotti G, Imperatori P, Paoletti AM and Pennesi G. Molecules 2021; 26: 1760. Crossref, Web of Science, Google Scholar
28. Ali H, St-Jean O, Tremblay-Morin J-P and van Lier JE. Tetrahedron Lett. 2006; 47: 8275–8278. Crossref, Web of Science, Google Scholar
29. Zanotti G, Angelini N, Mattioli G, Paoletti AM, Pennesi G, Caschera D, Sobolev AP, Beverina L, Calascibetta AM, Sanzone A, Di Carlo A, Berionni Berna B, Pescetelli S and Agresti A. ChemPlusChem 2020; 85: 2376–2386. Crossref, Web of Science, Google Scholar
30. Calvete M, Dias L, Henriques C, Pinto S, Carrilho R and Pereira M. Molecules 2017; 22: 741. Crossref, Web of Science, Google Scholar
31. Gomes C, Peixoto M and Pineiro M. J. Porphyr. Phthalocyanines 2019; 23: 889–897. Link, Web of Science, Google Scholar
32. Henriques CA, Pinto SMA, Aquino GLB, Pineiro M, Calvete MJF and Pereira MM. ChemSusChem 2014; 7: 2821–2824. Crossref, Web of Science, Google Scholar
33. Gomes C, Peixoto M and Pineiro M. Molecules 2021; 26: 6652. Crossref, Web of Science, Google Scholar
34. Pinto SMA, Henriques CA, Tomé VA, Vinagreiro CS, Calvete MJF, Daąbrowski JM, Piñeiro M, Arnaut LG and Pereira MM. J. Porphyr. Phthalocyanines 2016; 20: 45–60. Link, Web of Science, Google Scholar
35. Aken KV, Strekowski L and Patiny L. Beilstein J. Org. Chem. 2006; 2: 3. Google Scholar
36. Villemin D, Hammadi M, Hachemi M and Bar N. Molecules 2001; 6: 831–844. Crossref, Web of Science, Google Scholar
37. Chauhan S, Kumari P and Agarwal S. Synthesis 2007; 2007: 3713–3721. Crossref, Web of Science, Google Scholar
38. Osedach TP, Andrew TL and Bulović V. Energy Environ. Sci. 2013; 6: 711. Crossref, Web of Science, Google Scholar