Top

Published in:

01-11-2014 | Research Paper

β-(p-Carboxyaminophenyl)porphyrin derivatives: new dyes for TiO₂ dye-sensitized solar cells

Authors: Ana M. V. M. Pereira, Ana F. R. Cerqueira, Nuno M. M. Moura, Bernardo A. Iglesias, Maria A. F. Faustino, Maria G. P. M. S. Neves, José A. S. Cavaleiro, Mário J. C. Lima, António F. da Cunha

Published in: Journal of Nanoparticle Research | Issue 11/2014

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

New β-(p-carboxyaminophenyl)porphyrin derivatives were efficiently synthesized via palladium-catalysed amination of methyl 4-iodobenzoate with (2-amino-5-10,15,20-tetraphenylporphyrinato)nickel(II), followed by a demetallation/metallation sequence and basic hydrolysis. Optical and electrochemical studies revealed their potentiality for being considered as dyes in DSSCs devices, in which a power conversion efficiency of about 30 % of the more conventional Ru(II)-sensitizer N719 was achieved.

previous article Preparation and characterization of ZnO/graphene nanocomposite for improved photovoltaic performance

next article Evaluation of the efficiency of tumor and tissue delivery of carrier-mediated agents (CMA) and small molecule (SM) agents in mice using a novel pharmacokinetic (PK) metric: relative distribution index over time (RDI-OT)

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Available only for authorised users

Barea EM, Gónzalez-Pedro V, Ripollés-Sanchis T, Wu HP, Li LL, Yeh E, Diau EWG, Bisquert J (2011) Porphyrin dyes with high injection and low recombination for highly efficient mesoscopic dye-sensitized solar cells. J Phys Chem C 115:10898–10902. doi:10.1021/jp2018378 CrossRef

Benniston AC, Harriman A (2008) Artificial photosynthesis. Mater Today 11:26–34. doi:10.1016/S1369-7021(08)70250-5 CrossRef

Bessho T, Zakeeruddin SM, Yeh CY, Diau EWG, Grätzel M (2010) Highly efficient mesoscopic dye-sensitized solar cells based on donor-acceptor-substituted porphyrins. Angew Chem Int Ed 49:6646–6649. doi:10.1002/anie.201002118 CrossRef

Buchler JW (1975) Static coordination chemistry of metalloporphyrins. In: Smith KM (ed) Porphyrins and metalloporphyrins, chap 5. Elsevier, Amsterdam, pp 157–231

Campbell WM, Jolley KW, Wagner P, Wagner K, Walsh PJ, Gordon KC, Schmidt-Mende L, Nazeeruddin MK, Wang Q, Grätzel M, Officer DL (2007) Highly efficient porphyrin sensitizers for dye-sensitized solar cells. J Phys Chem C 111:11760–11762. doi:10.1021/jp0750598 CrossRef

Chapin DM, Fuller CS, Pearson GL (1954) A new silicon p-n junction photocell for converting solar radiation into electrical power. J Appl Phys 25:676. doi:10.1063/1.1721711 CrossRef

Chen CY, Wang M, Li JY, Pootrakulchote N, Alibabaei L, Ngoc-le C, Decoppet JD, Tsai JH, Grätzel C, Wu CG, Zakeeruddin SM, Grätzel M (2009) Highly efficient light-harvesting ruthenium sensitizer for thin-film dye-sensitized solar cells. ACS Nano 3:3103–3109. doi:10.1021/nn900756s CrossRef

Chen CY, Pootrakulchote N, Chen MY, Moehl T, Tsa HH, Zakeeruddin SM, Wu CG, Grätzel M (2012) A new heteroleptic ruthenium sensitizer for transparent dye-sensitized solar cells. Adv Energy Mater 2:1503–1509. doi:10.1002/aenm.201200285 CrossRef

Chu S, Majumdar A (2012) Opportunities and challenges for a sustainable energy future. Nature 484:294–303. doi:10.1038/nature11475 CrossRef

Clifford JN, Martínez-Ferrero E, Viterisi A, Palomares E (2011) Sensitizer molecular structure-device efficiency relationship in dye sensitized solar cells. Chem Soc Rev 40:1635–1646. doi:10.1039/B920664G CrossRef

D’Souza F, Ito O (2009) Supramolecular donor-acceptor hybrids of porphyrins/phthalocyanines with fullerenes/carbon nanotubes: electron transfer, sensing, switching, and catalytic applications. Chem Commun 33:4913–4928. doi:10.1039/B905753F CrossRef

Fields KB, Ruppel JV, Snyder NL, Zhang XP (2010) Porphyrin functionalization via palladium-catalyzed carbon–heteroatom cross-coupling reactions. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science, vol 3. World Scientific, Singapore, pp 367–428

Fukui N, Cha WY, Lee S, Tokuji S, Kim D, Yorimitsu H, Osuka A (2013) Oxidative fusion reactions of meso-(diarylamino)porphyrins. Angew Chem Int Ed 52:9728–9732. doi:10.1002/anie.201304794 CrossRef

Giraudeau A, Callot HJ, Jordan J, Ezhar I, Gross M (1979) Substituent effects in the electroreduction of porphyrins and metalloporphyrins. J Am Chem Soc 101:3857–3862. doi:10.1021/ja00508a024 CrossRef

Grätzel M (2003) Dye-sensitized solar cells. J Photochem Photobiol C 4:145–153. doi:10.1016/S1389-5567(03)00026-1 CrossRef

Green MA, Ho-Baillie A, Snaith HJ (2014) The emergence of perovskite solar cells. Nat Photonics 8:506–514. doi:10.1038/nphoton.2014.134 CrossRef

Hagfeldt A, Boschloo G, Sun L, Kloo L, Pettersson H (2010) Dye-sensitized solar cells. Chem Rev 110:6595–6663. doi:10.1021/cr900356p CrossRef

Hao F, Stoumpos CC, Cao DH, Chang RPH, Kanatzidis MG (2014) Lead-free solid-state organic-inorganic halide perovskite solar cells. Nat Photonics 8:489–494. doi:10.1038/nphoton.2014.82 CrossRef

Haumesser J, Pereira AMVM, Gisselbrecht JP, Merahi K, Choua S, Weiss J, Cavaleiro JAS, Ruppert R (2013) Inexpensive and efficient Ullmann methodology to prepare donor-substituted porphyrins. Org Lett 15:6282–6285. doi:10.1021/ol403132f CrossRef

Heo JH, Im SH, Noh JH, Mandal TN, Lim CS, Chang JA, Lee YH, Kim HJ, Sarkar A, Nazeeruddin MK, Grätzel M, Seok SI (2013) Efficient inorganic–organic hybrid heterojunction solar cells containing perovskite compound and polymeric hole conductors. Nat Photonics 7:486–491. doi:10.1038/nphoton.2013.80 CrossRef

Hombrecher HK, Gherdan VM, Ohm S, Cavaleiro JAS, Neves MGPMS, Condesso MF (1993) Synthesis and electrochemical investigation of β-alkyloxy substituted meso-tetraphenylporphyrins. Tetrahedron 49:8569–8578. doi:10.1016/S0040-4020(01)96263-5 CrossRef

Hsieh CP, Lu HP, Chiu CL, Lee CW, Chuang SH, Mai CL, Yen WN, Hsu SJ, Diau EWG, Yeh CY (2010) Synthesis and characterization of porphyrin sensitizers with various electron-donating substituents for highly efficient dye-sensitized solar cells. J Mater Chem 20:1127–1134. doi:10.1039/b919645e CrossRef

Im JH, Lee CR, Lee JW, Park SW, Park NG (2011) 6.5 % Efficient perovskite quantum-dot-sensitized solar cell. Nanoscale 3:4088–4093. doi:10.1039/c1nr10867k CrossRef

Imahori H, Matsubara Y, Iijima H, Umeyama T, Ito S, Niemi SM, Tkachenko NV, Lemmetyinen H (2010) Effects of meso-diarylamino group of porphyrins as sensitizers in dye-sensitized solar cells on optical, electrochemical, and photovoltaic properties. J Phys Chem C 114:10656–10665. doi:10.1021/jp102486b CrossRef

Ishida M, Park SW, Hwang D, Koo YB, Sessler JL, Kim DY, Kim D (2011) Donor-substituted β-functionalized porphyrin dyes on hierarchically structured mesoporous TiO₂ spheres. Highly efficient dye-sensitized solar cells. J Phys Chem C 115:19343–19354. doi:10.1021/jp202307b CrossRef

Ishida M, Hwang D, Koo YB, Sung J, Kim DY, Sessler JL, Kim D (2013) β-(Ethynylbenzoic acid)-substituted push–pull porphyrins: DSSC dyes prepared by a direct palladium-catalyzed alkynylation reaction. Chem Commun 49:9164–9166. doi:10.1039/C3CC44847A CrossRef

Ito A, Tanaka K (2010) Macrocyclic oligoarylamine-based spin system. Pure Appl Chem 82:979–989. doi:10.1351/pac-con-09-10-16 CrossRef

Jones BA, Facchetti A, Wasielewski MR, Marks TJ (2007) Tuning orbital energetics in arylene diimide semiconductors. Materials design for ambient stability of n-type charge transport. J Am Chem Soc 129:15259–15278. doi:10.1021/ja075242e CrossRef

Kim HS, Lee CR, Im JH, Lee KB, Moehl T, Marchioro A, Moon SJ, Humphry-Baker R, Yum JH, Moser JE, Grätzel M, Park NG (2012) Lead iodide perovskite sensitized all-solid-state submicron thin film mesoscopic solar cell with efficiency exceeding 9 %. Sci Rep 2:591. doi:10.1038/srep00591

Kojima A, Teshima K, Shirai Y, Miyasaka T (2009) Organometal halide perovskites as visible-light sensitizers for photovoltaic cells. J Am Chem Soc 131:6050–6051. doi:10.1021/ja809598r CrossRef

Lee CW, Lu HP, Lan CM, Huang YL, Liang YR, Yen WN, Liu YC, Lin YS, Diau EWG, Yeh CY (2009) Novel zinc porphyrin sensitizers for dye-sensitized solar cells: synthesis and spectral, electrochemical, and photovoltaic properties. Chem Eur J 15:1403–1412. doi:10.1002/chem.200801572 CrossRef

Lee MM, Teuscher J, Miyasaka T, Murakami TN, Snaith HJ (2012) Efficient hybrid solar cells based on meso-superstructured organometal halide perovskites. Science 338:643–647. doi:10.1126/science.1228604 CrossRef

Lenzmann F, Krueger J, Burnside S, Brooks K, Grätzel M, Gal D, Rühle S, Cahen D (2011) Hydration properties of α-, β-, and γ-cyclodextrins from molecular dynamics simulations. J Phys Chem B 105:6347–6357. doi:10.1021/jp2013946 CrossRef

Li LL, Diau EWG (2013) Porphyrin-sensitized solar cells. Chem Soc Rev 42:291–304. doi:10.1039/C2CS35257E CrossRef

Liu D, Kelly TL (2014) Perovskite solar cells with a planar heterojunction structure prepared using room-temperature solution processing techniques. Nat Photonics 8:133–138. doi:10.1038/nphoton.2013.342 CrossRef

Liu C, Shen DM, Chen QY (2007) Practical and efficient synthesis of various meso-functionalized porphyrins via simple ligand-free nickel-catalyzed C–O, C–N, and C–C cross-coupling reactions. J Org Chem 72:2732–2736. doi:10.1021/jo0618728 CrossRef

Lo PC, Leng X, Ng DPK (2007) Hetero-arrays of porphyrins and phthalocyanines. Coord Chem Rev 251:2334–2353. doi:10.1016/j.ccr.2007.03.007 and references thereinCrossRef

Mathew S, Yella A, Gao P, Humphry-Baker R, Curchod BFE, Ashari-Astani N, Tavernelli I, Rothlisberger U, Nazeeruddin MK, Grätzel M (2014) Dye-sensitized solar cells with 13 % efficiency achieved through the molecular engineering of porphyrin sensitizers. Nat Chem 6:242–247. doi:10.1038/nchem.1861 CrossRef

Mei A, Li X, Liu L, Ku Z, Liu T, Rong Y, Xu M, Hu M, Chen J, Yang Y, Grätzel M, Han H (2014) A hole-conductor-free, fully printable mesoscopic perovskite solar cell with high stability. Science 345:295–298. doi:10.1126/science.1254763 CrossRef

Mishra A, Fischer MKR, Bäuerle P (2009) Metal-free organic dyes for dye-sensitized solar cells: from structure: property relationships to design rules. Angew Chem Int Ed 48:2474–2499. doi:10.1002/anie.200804709 CrossRef

Moura NMM, Faustino MAF, Neves MGPMS, Tomé AC, Rakib EM, Hannioui A, Mojahidi S, Hackbarth S, Röder B, Paz FAA, Silva AMS, Cavaleiro JAS (2012) Novel pyrazoline and pyrazole porphyrin derivatives: synthesis and photophysical properties. Tetrahedron 68:8181–8183. doi:10.1016/j.tet.2012.07.0721 CrossRef

Nazeeruddin MK, Kay A, Rodicio I, Humphry-Baker R, Muller E, Liska P, Vlachopoulos N, Grätzel M (1993) Conversion of light to electricity by cis-X₂bis(2,2′-bipyridyl-4,4′-dicarboxylate)ruthenium(II) charge-transfer sensitizers (X = Cl−, Br−, I−, CN−, and SCN−) on nanocrystalline titanium dioxide electrodes. J Am Chem Soc 115:6382–6390. doi:10.1021/ja00067a063 CrossRef

Nazeeruddin MK, Klein C, Liska P, Grätzel M (2005) Synthesis of novel ruthenium sensitizers and their application in dye-sensitized solar cells. Coord Chem Rev 249:1460–1467. doi:10.1016/j.ccr.2005.03.025 CrossRef

Noel NK, Stranks SD, Abate A, Wehrenfennig C, Guarnera S, Haghighirad AA, Sadhanala A, Eperon GE, Pathak SK, Johnston MB, Petrozza A, Herza LM, Snaith HJ (2014) Lead-free organic-inorganic tin halide perovskites for photovoltaic applications. Energy Environ Sci 7:3061–3068. doi:10.1039/c4ee01076k CrossRef

O’Regan B, Grätzel M (1991) A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO₂ films. Nature 353:737–740. doi:10.1038/353737a0 CrossRef

Pereira AMVM, Alonso CMA, Neves MGPMS, Tomé AC, Silva AMS, Paz FAA, Cavaleiro JAS (2008) A new synthetic approach to N-arylquinolino[2,3,4-at]porphyrins from β-arylaminoporphyrins. J Org Chem 73:7353–7356. doi:10.1021/jo800975c CrossRef

Pereira AMVM, Soares ARM, Hausmann A, Neves MGPMS, Tomé AC, Silva AMS, Cavaleiro JAS, Guldi DM, Torres T (2011a) Distorted fused porphyrin–phthalocyanine conjugates: synthesis and photophysics of supramolecular assembled systems with a pyridylfullerene. Phys Chem Chem Phys 13:11858–11863. doi:10.1039/C1CP00016K CrossRef

Pereira AMVM, Neves MGPMS, Cavaleiro JAS, Jeandon C, Gisselbrecht JP, Choua S, Ruppert R (2011b) Diporphyrinylamines: synthesis and electrochemistry. Org Lett 13:4742–4745. doi:10.1021/ol2020658 CrossRef

Pereira AMVM, Hausmann A, Tomé JPC, Trukhina O, Urbani M, Neves MGPMS, Cavaleiro JAS, Guldi DM, Torres T (2012) Porphyrin–phthalocyanine/pyridylfullerene supramolecular assemblies. Chem Eur J 18:3210–3219. doi:10.1002/chem.201103776 CrossRef

Ripollés-Sanchis T, Guo BC, Wu HP, Pan TY, Lee HW, Raga SR, Fabregat-Santiago F, Bisquert J, Yeh CY, Diau EWG (2012) Design and characterization of alkoxy-wrapped push–pull porphyrins for dye-sensitized solar cells. Chem Commun 48:4368–4370. doi:10.1039/c2cc31111a CrossRef

Rocha Gonsalves AMd’A, Varejão JMTB, Pereira MM (1991) Some new aspects related to the synthesis of meso-substituted porphyrins. J Heterocycl Chem 28:635–640. doi:10.1002/jhet.5570280317 CrossRef

Smith KM, Milgrom LR, Kenner GW (1981) Syntheses of monofunctional porphyrinyl peptides containing glycine and leucine. J Chem Soc, Perkin Trans 1 2065–2069. doi:10.1039/P19810002065

Snaith HJ (2013) Perovskites: the emergence of a new era for low-cost, high-efficiency solar cells. J Phys Chem Lett 4:3623–3630. doi:10.1021/jz4020162 CrossRef

Wang CL, Lan CM, Hong SH, Wang YF, Pan TY, Chang CW, Kuo HH, Kuo MY, Diau EWG, Lin CY (2012) Enveloping porphyrins for efficient dye-sensitized solar cells. Energy Environ Sci 5:6933–6940. doi:10.1039/c2ee03308a CrossRef

Wang Y, Li X, Liu B, Wu W, Zhu W, Xie Y (2013) Porphyrins bearing long alkoxyl chains and carbazole for dye-sensitized solar cells: tuning cell performance through an ethynylene bridge. RSC Adv 3:14780–14790. doi:10.1039/C3RA40788H CrossRef

Wasielewski MR (1992) Photoinduced electron transfer in supramolecular systems for artificial photosynthesis. Chem Rev 92:435–461. doi:10.1021/cr00011a005 CrossRef

Wu SL, Lu HP, Yu HT, Chuang SH, Chiu CL, Lee CW, Diau EWG, Yeh CY (2010) Design and characterization of porphyrin sensitizers with a push-pull framework for highly efficient dye-sensitized solar cells. Energy Environ Sci 3:949–955. doi:10.1039/c003872p CrossRef

Yella A, Lee HW, Tsao HN, Yi C, Chandiran AK, Nazeeruddin MK, Diau EWG, Yeh CY, Zakeeruddin SM, Grätzel M (2011) Porphyrin-sensitized solar cells with cobalt (II/III)–based redox electrolyte exceed 12 percent efficiency. Science 334:629–634. doi:10.1126/science.1209688 CrossRef

Title: β-(p-Carboxyaminophenyl)porphyrin derivatives: new dyes for TiO2 dye-sensitized solar cells
Authors: Ana M. V. M. Pereira
Ana F. R. Cerqueira
Nuno M. M. Moura
Bernardo A. Iglesias
Maria A. F. Faustino
Maria G. P. M. S. Neves
José A. S. Cavaleiro
Mário J. C. Lima
António F. da Cunha
Publication date: 01-11-2014
Publisher: Springer Netherlands
Published in: Journal of Nanoparticle Research / Issue 11/2014
Print ISSN: 1388-0764
Electronic ISSN: 1572-896X
DOI: https://doi.org/10.1007/s11051-014-2647-0

Springer Professional

Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 11/2014

Ligands influence a carbon nanotube penetration through a lipid bilayer

Synthesis and characterization of gadolinium nanosheets with bound rose bengal: potential use in photodynamic therapy and MRI

Optical investigation of diffusion of single Ag markers in confined water films

Effect of magnetocrystalline anisotropy on the magnetic properties of electrodeposited Co–Pt nanowires

Adsorption at cell surface and cellular uptake of silica nanoparticles with different surface chemical functionalizations: impact on cytotoxicity

Synthesis of core–shell nanostructured magnetic photocatalyst Fe3O4@SiO2@Ag3PO4 with excellent visible-light-responding photocatalytic activity

Premium Partners