A DFT study on natural sensitizers with donor-π-acceptor architecture based on 1,7-diazaheptametine for applications in Dye-Sensitized Solar Cells (DSSC)

Lopera A; Vélez E; Restrepo J; Polo V.

doi:10.1016/j.comptc.2023.114450

A DFT study on natural sensitizers with donor-π-acceptor architecture based on 1,7-diazaheptametine for applications in Dye-Sensitized Solar Cells (DSSC)

dc.contributor.affiliation	Lopera, A., Facultad de Ciencias Básicas, Universidad de Medellín, Medellín, Colombia, Facultad de Ingenierías, Corporación Universitaria Minuto de Dios, UNIMINUTO, Bello, Colombia
dc.contributor.affiliation	Vélez, E., Facultad de Ciencias Básicas, Universidad de Medellín, Medellín, Colombia
dc.contributor.affiliation	Restrepo, J., Facultad de Ciencias Básicas, Universidad de Medellín, Medellín, Colombia
dc.contributor.affiliation	Polo, V., Departamento de Química Física and Instituto de Biocomputación y Física de Sistemas Complejos (BIFI), Universidad de Zaragoza, Zaragoza, Spain
dc.contributor.author	Lopera A
dc.contributor.author	Vélez E
dc.contributor.author	Restrepo J
dc.contributor.author	Polo V.
dc.date.accessioned	2024-07-31T21:06:48Z
dc.date.available	2024-07-31T21:06:48Z
dc.date.issued	2024
dc.description	Nature offers a wide range of organic dyes with potential as sensitizers in DSSC technology. Among them, some natural dyes contain a 1,7-diazaheptamethine system, influencing their chromatic properties. In this investigation, we computationally analyzed 21 natural betalain dyes featuring a common structural moiety through Density Functional Theory calculations. Among them, eight dyes were classified under the betacyanin subfamily, while the remaining thirteen were attributed to the betaxanthin subfamily. These dyes were examined both in isolation and when bound to titanium dioxide (dye@TiO2). The betaxanthin subfamily showed more twisted geometries, while the betacyanin subfamily exhibited a smaller energy gap. All isolated dyes or dyes@TiO2 exhibit maximum absorption peaks within the visible region (350–700 nm), showcasing their light-capturing capacity. Stability, evidenced by negative adsorption energies, suggests the spontaneity of the adsorption process. Furthermore, our results indicate that the nature of bonding significantly influences the electronic properties of dye@TiO2 complexes. Collectively, these results underscore the importance of the 1,7-diazaheptamethine system in imparting color and structure to these dyes. Our thorough analysis, encompassing molecular interactions, geometric attributes—especially the configuration of donor groups—electronic properties, and absorption spectra, provides valuable insights into the potential applications and effectiveness of these dyes for incorporation in dye-sensitized solar cells (DSSC). © 2023 Elsevier B.V.
dc.identifier.doi	10.1016/j.comptc.2023.114450
dc.identifier.instname	instname:Universidad de Medellín	spa
dc.identifier.issn	2210271X
dc.identifier.reponame	reponame:Repositorio Institucional Universidad de Medellín	spa
dc.identifier.repourl	repourl:https://repository.udem.edu.co/
dc.identifier.uri	http://hdl.handle.net/11407/8395
dc.language.iso	eng
dc.publisher	Elsevier B.V.	spa
dc.publisher.faculty	Facultad de Ciencias Básicas	spa
dc.relation.citationvolume	1232
dc.relation.isversionof	https://www.scopus.com/inward/record.uri?eid=2-s2.0-85182424697&doi=10.1016%2fj.comptc.2023.114450&partnerID=40&md5=c774e08dd152f1859b373e8a475924ff
dc.relation.references	Alwin, S., Sahaya Shajan, X., Aerogels: promising nanostructured materials for energy conversion and storage applications (2020) Mater. Renew. Sustain Energy, 9, p. 7
dc.relation.references	Petrova-Koch, V., Hezel, R., Goetzberger, A., High-Efficient Low-Cost Photovoltaics (2020), Springer International Publishing Cham
dc.relation.references	Błaszczyk, A., Joachimiak-Lechman, K., Sady, S., Environmental performance of dye-sensitized solar cells based on natural dyes (2021) Sol. Energy, 215, pp. 346-355
dc.relation.references	Freitag, M., Teuscher, J., Saygili, Y., Dye-sensitized solar cells for efficient power generation under ambient lighting (2017) Nat. Photon., 11, pp. 372-378
dc.relation.references	Devadiga, D., Selvakumar, M., Shetty, P., Santosh, M.S., Dye-sensitized solar cell for indoor applications: a mini-review (2021) J. Electron. Mater., 50, pp. 3187-3206
dc.relation.references	Kakiage, K., Aoyama, Y., Yano, T., Highly-efficient dye-sensitized solar cells with collaborative sensitization by silyl-anchor and carboxy-anchor dyes (2015) Chem. Commun., 51, pp. 15894-15897
dc.relation.references	Tripathi, A., Ganjoo, A., Chetti, P., Influence of internal acceptor and thiophene based π-spacer in D-A-π-A system on photophysical and charge transport properties for efficient DSSCs: A DFT insight (2020) Sol. Energy, 209, pp. 194-205
dc.relation.references	Tripathi, A., Kumar, V., Chetti, P., Impact of internal (donor/acceptor) moieties and π-spacer in triphenylamine-based dyes for DSSCs (2022) J. Photochem. Photobiol. A Chem., 426
dc.relation.references	Jiang, H., Wu, Y., Islam, A., Molecular engineering of quinoxaline-based D-A−π–A organic sensitizers: taking the merits of a large and rigid auxiliary acceptor (2018) ACS Appl. Mater. Interfaces, 10, pp. 13635-13644
dc.relation.references	Namuangruk, S., Fukuda, R., Ehara, M., D-D−π–A-type organic dyes for dye-sensitized solar cells with a potential for direct electron injection and a high extinction coefficient: synthesis, characterization, and theoretical investigation (2012) J. Phys. Chem. C, 116, pp. 25653-25663
dc.relation.references	Singh, M., Kurchania, R., Pockett, A., Characterization of metal-free D-(π-A)2 organic dye and its application as cosensitizer along with N719 dye for efficient dye-sensitized solar cells (2015) Ind. J. Phys., 89, pp. 1041-1050
dc.relation.references	Xia, H.-Q., Kong, C.-P., Wang, J., Design of D-A–π–A organic dyes with different acceptor and auxiliary acceptor for highly efficient dye-sensitized solar cells: a computational study (2014) RSC Adv., 4, pp. 50338-50350
dc.relation.references	Yang, W., Cao, D., Zhang, H., Dye-sensitized solar cells based on (D−π−A)3L2 phenothiazine dyes containing auxiliary donors and flexible linkers with different length of carbon chain (2018) Electrochim. Acta, 283, pp. 1732-1741
dc.relation.references	Li, P., Zhang, H., Troisi, A., Systematic study of the effect of auxiliary acceptors in D-A′−π–A sensitizers used on dye-sensitized solar cells (2018) J. Phys. Chem. C, 122, pp. 23890-23898
dc.relation.references	Arkan, F., Izadyar, M., Theoretical prediction of voltage-current behavior and other photovoltaic properties of natural flavonoid-based solar cells (2021) Sol. Energy, 228, pp. 89-99
dc.relation.references	Cherepy, N.J., Smestad, G.P., Grätzel, M., Zhang, J.Z., Ultrafast electron injection: implications for a photoelectrochemical cell utilizing an anthocyanin dye-sensitized TiO 2 nanocrystalline electrode (1997) J. Phys. Chem. B, 101, pp. 9342-9351
dc.relation.references	Teoli, F., Lucioli, S., Nota, P., Role of pH and pigment concentration for natural dye-sensitized solar cells treated with anthocyanin extracts of common fruits (2016) J. Photochem. Photobiol. A Chem., 316, pp. 24-30
dc.relation.references	Orona-Navar, A., Aguilar-Hernández, I., Cerdán-Pasarán, A., Astaxanthin from Haematococcus pluvialis as a natural photosensitizer for dye-sensitized solar cell (2017) Algal Res., 26, pp. 15-24
dc.relation.references	Sreeja, S., Pesala, B., Performance enhancement of betanin solar cells co-sensitized with indigo and lawsone: a comparative study (2019) ACS Omega, 4, pp. 18023-18034
dc.relation.references	Santhanamoorthi, N., Lo, C.M., Jiang, J.C., Molecular design of porphyrins for dye-sensitized solar cells: a DFT/TDDFT study (2013) J. Phys. Chem. Lett., 4, pp. 524-530
dc.relation.references	Zarate, X., González, P.I., Caramori, S., Experimental and DFT study of natural curcumin derived dyes as n-type sensitizers (2021) Sol. Energy, 225, pp. 305-315
dc.relation.references	Isah, K.U., Ahmadu, U., Idris, A., Betalain pigments as natural photosensitizers for dye-sensitized solar cells: the effect of dye pH on the photoelectric parameters (2015) Mater. Renew. Sust. Energy, 4
dc.relation.references	Ramamoorthy, R., Radha, N., Maheswari, G., Betalain and anthocyanin dye-sensitized solar cells (2016) J. Appl. Electrochem., 46, pp. 929-941
dc.relation.references	Qin, C., Clark, A.E., DFT characterization of the optical and redox properties of natural pigments relevant to dye-sensitized solar cells (2007) Chem. Phys. Lett., 438, pp. 26-30
dc.relation.references	Mérillon, J.-M., Ramawat, K.G., Bioactive Molecules in Food (2020), Springer International Publishing Cham
dc.relation.references	Rahimi, P., Abedimanesh, S., Mesbah-Namin, S.A., Ostadrahimi, A., Betalains, the nature-inspired pigments, in health and diseases (2019) Crit. Rev. Food Sci. Nutr., 59, pp. 2949-2978
dc.relation.references	Akbar Hussain, E., Sadiq, Z., Zia-Ul-Haq, M., Betalains: Biomolecular Aspects (2018), Springer International Publishing Cham
dc.relation.references	Piattelli, M., Minale, L., Pigments of centrospermae—II (1964) Phytochemistry, 3, pp. 547-557
dc.relation.references	Gandía-Herrero, F., Jiménez-Atiénzar, M., Cabanes, J., Stabilization of the bioactive pigment of Opuntia fruits through maltodextrin encapsulation (2010) J. Agric. Food Chem., 58, pp. 10646-10652
dc.relation.references	Belhadj Slimen, I., Najar, T., Abderrabba, M., Chemical and antioxidant properties of betalains (2017) J. Agric. Food Chem., 65, pp. 675-689
dc.relation.references	Kumorkiewicz-Jamro, A., Świergosz, T., Sutor, K., Multi-colored shades of betalains: recent advances in betacyanin chemistry (2021) Nat. Prod. Rep., 38, pp. 2315-2346
dc.relation.references	Zhang, L., Cole, J.M., Anchoring groups for dye-sensitized solar cells (2015) ACS Appl. Mater. Interfaces, 7, pp. 3427-3455
dc.relation.references	Frisch, M.J., Trucks, G.W., (2013), Gaussian 09, Revision D.01. H.B. Schlegel
dc.relation.references	Becke, A.D., Density-functional thermochemistry. III. The role of exact exchange (1993) J. Chem. Phys., 98, pp. 5648-5652
dc.relation.references	Lee, C., Yang, W., Parr, R.G., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density (1988) Phys. Rev. B, 37, pp. 785-789
dc.relation.references	Yanai, T., Tew, D.P., Handy, N.C., A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP) (2004) Chem. Phys. Lett., 393, pp. 51-57
dc.relation.references	He, L.-J., Sun, Y., Li, W., Highly-efficient sensitizer with zinc porphyrin as building block: insights from DFT calculations (2018) Sol. Energy, 173, pp. 283-290
dc.relation.references	Li, Y., Li, X., Xu, Y., Theoretical screening of high-efficiency sensitizers with D-π-A framework for DSSCs by altering promising donor group (2020) Sol. Energy, 196, pp. 146-156
dc.relation.references	Samanta, P.N., Majumdar, D., Roszak, S., Leszczynski, J., First-principles approach for assessing cold electron injection efficiency of dye-sensitized solar cell: elucidation of mechanism of charge injection and recombination (2020) J. Phys. Chem. C, 124, pp. 2817-2836
dc.relation.references	Singh, M., Kanaparthi, R.K., Theoretical exploration of 1,3-Indanedione as electron acceptor-cum-anchoring group for designing sensitizers towards DSSC applications (2022) Sol. Energy, 237, pp. 456-469
dc.relation.references	Cancès, E., Mennucci, B., Tomasi, J., A new integral equation formalism for the polarizable continuum model: theoretical background and applications to Isotropic and anisotropic dielectrics (1997) J. Chem. Phys., 107
dc.relation.references	Chen, H., Gong, Y., Vázquez-Mayagoitia, Á., Dye aggregation, photostructural reorganization and multiple concurrent dye···TiO 2 binding modes in dye-sensitized solar cell working electrodes containing benzothiadiazole-based dye RK-1 (2020) ACS Appl. Energy Mater., 3, pp. 423-430
dc.relation.references	Sánchez-de-Armas, R., San Miguel, M.Á., Oviedo, J., Sanz, J.F., Coumarin derivatives for dye sensitized solar cells: a TD-DFT study (2012) PCCP, 14, pp. 225-233
dc.relation.references	Fadili, D., Bouzzine, S.M., Hamidi, M., Study of the structural and optoelectronic properties of dye solar cells based on phosphonic acid anchoring by DFT functionals (2021) New J. Chem., 45, pp. 2723-2733
dc.relation.references	Sánchez-de-Armas, R., Oviedo, J., San Miguel, M.Á., Sanz, J.F., Direct vs indirect mechanisms for electron injection in dye-sensitized solar cells (2011) J. Phys. Chem. C, 115, pp. 11293-11301
dc.relation.references	Weigend, F., Ahlrichs, R., Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy (2005) PCCP, 7, p. 3297
dc.relation.references	Shockley, W., Queisser, H.J., Detailed balance limit of efficiency of p-n junction solar cells (1961) J. Appl. Phys., 32, pp. 510-519
dc.relation.references	Manzoor, T., Niaz, S., Pandith, A.H., Exploring the effect of different coumarin donors on the optical and photovoltaic properties of azo-bridged push-pull systems: a theoretical approach (2019) Int. J. Quantum Chem, 119
dc.relation.references	Manzoor, T., Asmi, S., Niaz, S., Hussain Pandith, A., Computational studies on optoelectronic and charge transfer properties of some perylene-based donor-π-acceptor systems for dye sensitized solar cell applications (2017) Int. J. Quantum Chem, 117, p. e25332
dc.relation.references	Manzoor, T., Pandith, A.H., Theoretical studies on the structure, optoelectronic and photosensitizer applications of NKX class of coumarin dye molecules (2018) ChemistrySelect, 3, pp. 2376-2385
dc.relation.references	Mohr, T., Aroulmoji, V., Ravindran, R.S., DFT and TD-DFT study on geometries, electronic structures and electronic absorption of some metal free dye sensitizers for dye sensitized solar cells (2015) Spectrochim. Acta A Mol. Biomol. Spectrosc., 135, pp. 1066-1073
dc.relation.references	Wu, Z., Fan, B., Xue, F., Organic molecules based on dithienyl-2,1,3-benzothiadiazole as new donor materials for solution-processed organic photovoltaic cells (2010) Sol. Energy Mater. Sol. Cells, 94, pp. 2230-2237
dc.relation.references	Boschloo, G., Hagfeldt, A., Characteristics of the iodide/triiodide redox mediator in dye-sensitized solar cells (2009) Acc. Chem. Res., 42, pp. 1819-1826
dc.relation.references	Fan, W., Tan, D., Deng, W.-Q., Acene-modified triphenylamine dyes for dye-sensitized solar cells: a computational study (2012) ChemPhysChem, 13, pp. 2051-2060
dc.relation.references	Nazeeruddin, M.K., Kay, A., Rodicio, I., 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 (1993) J. Am. Chem. Soc., 115, pp. 6382-6390
dc.relation.references	Zhang, C.-R., Liu, L., Zhe, J.-W., The role of the conjugate bridge in electronic structures and related properties of tetrahydroquinoline for dye sensitized solar cells (2013) Int. J. Mol. Sci., 14, pp. 5461-5481
dc.relation.references	Chaitanya, K., Ju, X.H., Heron, B.M., Theoretical study on the light harvesting efficiency of zinc porphyrin sensitizers for DSSCs (2014) RSC Adv., 4, pp. 26621-26634
dc.relation.references	Zhang, J., Kan, Y.H., Bin, L.H., How to design proper π-spacer order of the D-π-A dyes for DSSCs? A density functional response (2012) Dyes Pigm., 95, pp. 313-321
dc.relation.references	Manzoor, T., Pandith, A.H., Enhancing the photoresponse by CdSe-Dye-TiO 2 -based multijunction systems for efficient dye-sensitized solar cells: a theoretical outlook (2019) J. Comput. Chem., 40, pp. 2444-2452
dc.relation.references	Preat, J., Jacquemin, D., Michaux, C., Perpète, E.A., Improvement of the efficiency of thiophene-bridged compounds for dye-sensitized solar cells (2010) Chem. Phys., 376, pp. 56-68
dc.relation.references	Koopmans, T., Über die zuordnung von wellenfunktionen und eigenwerten zu den einzelnen elektronen eines atoms (1934) Physica, 1, pp. 104-113
dc.relation.references	Preat, J., Michaux, C., Jacquemin, D., Perpète, E.A., Enhanced efficiency of organic dye-sensitized solar cells: triphenylamine derivatives (2009) J. Phys. Chem. C, 113, pp. 16821-16833
dc.relation.references	Daeneke, T., Mozer, A.J., Uemura, Y., Dye regeneration kinetics in dye-sensitized solar cells (2012) J. Am. Chem. Soc., 134, pp. 16925-16928
dc.relation.references	Lee, W., Yuk, S.B., Choi, J., The effects of the number of anchoring groups and N-substitution on the performance of phenoxazine dyes in dye-sensitized solar cells (2014) Dyes Pigm., 102, pp. 13-21
dc.relation.references	Wang, Z., Liang, M., Hao, Y., Influence of the N-heterocycle substituent of the dithieno[3,2-b:2′,3′-d]pyrrole (DTP) spacer as well as sensitizer adsorption time on the photovoltaic properties of arylamine organic dyes (2013) J. Mater. Chem. A Mater., 1, p. 11809
dc.relation.references	Yang, Z., Liu, Y., Liu, C., TDDFT screening auxiliary withdrawing group and design the novel D-A-π-A organic dyes based on indoline dye for highly efficient dye-sensitized solar cells (2016) Spectrochim. Acta A Mol. Biomol. Spectrosc., 167, pp. 127-133
dc.relation.references	Singh, M., Nadendla, S., Kanaparthi, R.K., Unravelling the effect of donor-π-acceptor architecture in designing 1,3-indanedione based sensitizers for DSSC applications (2023) J. Photochem. Photobiol. A Chem., 435
dc.relation.references	He, L., Guo, Y., Kloo, L., The dynamics of light-induced interfacial charge transfer of different dyes in dye-sensitized solar cells studied by ab initio molecular dynamics (2021) PCCP, 23, pp. 27171-27184
dc.relation.references	Sen, A., Groß, A., Does involving additional linker always increase the efficiency of an organic dye for p -type dye-sensitized solar cells? (2019) ACS Appl Energy Mater, 2, pp. 6341-6347
dc.relation.references	Ma, W., Jiao, Y., Meng, S., Predicting energy conversion efficiency of dye solar cells from first principles (2014) J. Phys. Chem. C, 118, pp. 16447-16457
dc.relation.references	Grätzel, M., Conversion of sunlight to electric power by nanocrystalline dye-sensitized solar cells (2004) J. Photochem. Photobiol. A Chem., 164, pp. 3-14
dc.relation.references	Estrella, L.L., Balanay, M.P., Kim, D.H., The effect of donor group rigidification on the electronic and optical properties of arylamine-based metal-free dyes for dye-sensitized solar cells: a computational study (2016) Chem. A Eur. J., 120, pp. 5917-5927
dc.relation.references	El Mouhi, R., Slimi, A., Fitri, A., DFT, DFTB and TD-DFT theoretical investigations of π-conjugated molecules based on thieno[2,3-b] indole for dye-sensitized solar cell applications (2022) Phys. B Condens Matter, 636
dc.relation.references	Anselmi, C., Mosconi, E., Pastore, M., Adsorption of organic dyes on TiO2 surfaces in dye-sensitized solar cells: interplay of theory and experiment (2012) PCCP, 14, p. 15963
dc.relation.references	Prajongtat, P., Suramitr, S., Nokbin, S., Density functional theory study of adsorption geometries and electronic structures of azo-dye-based molecules on anatase TiO2 surface for dye-sensitized solar cell applications (2017) J. Mol. Graph. Model., 76, pp. 551-561
dc.relation.references	Pelet, S., Moser, J.-E., Grätzel, M., Cooperative effect of adsorbed cations and iodide on the interception of back electron transfer in the dye sensitization of nanocrystalline TiO 2 (2000) J. Phys. Chem. B, 104, pp. 1791-1795
dc.relation.references	Wang, Z.-S., Li, F.-Y., Huang, C.-H., Photocurrent enhancement of hemicyanine dyes containing RSO 3 - group through treating TiO 2 films with hydrochloric acid (2001) J. Phys. Chem. B, 105, pp. 9210-9217
dc.relation.references	Fu, Y., Lu, T., Xu, Y., Theoretical screening and design of SM315-based porphyrin dyes for highly efficient dye-sensitized solar cells with near-IR light harvesting (2018) Dyes Pigm., 155, pp. 292-299
dc.relation.references	Tseng, C.-M., Lee, Y.T., Ni, C.-K., Photodissociation dynamics of N -methylindole, N-methylpyrrole, and anisole (2009) Chem. A Eur. J., 113, pp. 3881-3885
dc.rights.accessrights	info:eu-repo/semantics/restrictedAccess
dc.source	Computational and Theoretical Chemistry
dc.source	Comput. Theor. Chem.
dc.source	Scopus
dc.subject	1,7-Diazaheptamethin system	eng
dc.subject	Betalains	eng
dc.subject	DFT	eng
dc.subject	DSSC sensitizers	eng
dc.subject	Natural dyes	eng
dc.subject	Photovoltaic parameters	eng
dc.title	A DFT study on natural sensitizers with donor-π-acceptor architecture based on 1,7-diazaheptametine for applications in Dye-Sensitized Solar Cells (DSSC)	eng
dc.type	article
dc.type.local	Artículo	spa
dc.type.version	info:eu-repo/semantics/publishedVersion

Colecciones

Indexados Scopus

A DFT study on natural sensitizers with donor-π-acceptor architecture based on 1,7-diazaheptametine for applications in Dye-Sensitized Solar Cells (DSSC)

Archivos

Colecciones