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  • Phthalocyanines, subphthalocyanines, porphyrins, and beyond: A journey from solution studies to on-surface synthesis

Phthalocyanines, subphthalocyanines, porphyrins, and beyond: A journey from solution studies to on-surface synthesis

Prof. Giovanni Bottari (UAM / IMDEA Nanociencia)
Conference Room, IMDEA Nanociencia
Tuesday, 17 June 2025 12:00

Place: Conference Room, IMDEA Nanociencia

Abstract: 

Phthalocyanines (Pcs)[1a] and subphthalocyanines (SubPcs)[1b] are aromatic macrocycles that possess a planar and a bowl-shape structure, respectively, while sharing interesting optoelectronic features such as a broad and intense optical absorption and a rich redox chemistry, properties which can be fine-tuned by varying the nature of the macrocycles’ peripheral and/or axial substituents. As a consequence of their synthetic versatility and unique physical properties, these two macrocycles have been widely employed as building blocks for the preparation of molecular and supramolecular electron donor-acceptor (D-A) ensembles in which photoinduced energy/electron transfer events can be triggered/modulated as a function of the electronic character of the macrocycles’ counterpart(s).[2]

In the first part of my talk, I will present some selected examples of the preparation and study of D-A systems based on Pcs, SubPcs, and other porphyrinoids in which the macrocycles have been connected to molecular species with interesting structural and electronic features such as, for example, C60 fullerene,[3a] endohedral metallofullerenes,[3b] tetracyanobuta-1,3-diene,[3c,d,e,f] or cyclopenta[hi]aceanthrylene.[3g]

In the second part of my presentation, I will offer an overview on our current effort towards the preparation of porphyrin (Por)-based nanoarchitectures fabricated by on-surface synthesis. During the last decade, on-surface synthesis has emerged as a powerful tool for the construction of large, planar, π-conjugated structures that are not accessible through standard solution chemistry.[4] Among the building blocks used for the fabrication of such surface-supported nanoarchitectures, Pors are of particular interest due to their planar structure with an aromatic core of 18 π-electrons, remarkable thermal stability, and tuneable redox properties. In this context, I will present some recent examples of the on-surface fabrication, and structural and electronic characterization of some novel Por-graphene nanoribbon hybrids,[5a,c] monomeric π-extended Pors,[5b,e] Por nanotapes,[5d] and metalo-organic Por nanochains.[5f]

References:

1.   a) Bottari, G. et al. Chem. Rev. 2010, 110, 6768; b) Lavarda, et al. Chem. Soc. Rev. 2022, 51, 9482.
2.  Bottari, G. et al. Coord. Chem. Rev. 2021, 428, 213605.
3.   a) Bottari G. et al. Angew. Chem. Int. Ed. 2016, 55, 11020; b) Trukhina, O. et al. J. Am. Chem. Soc. 2015, 137, 12914; c) Sekita, M. et al. Angew. Chem. Int. Ed. 2016, 55, 5560; d) Winterfeld, K. A. et al. J. Am. Chem. Soc. 2017, 139, 5520; e) K. A. Winterfeld, et al. Chem. Sci. 2019, 10, 10997; f) Lavarda, G. et al. Angew. Chem. Int. Ed. 2020, 59, 21224; f) Schierl, C. et al. G. Angew. Chem. Int. Ed. 2019, 58, 14644.
4.   Clair, S.; de Oteyza, D. G. Chem. Rev. 2019, 119, 4717.
5.   a) Mateo, L. M. et al. Angew. Chem. Int. Ed. 2020, 59, 1334; b) Sun, Q. et al. J. Am. Chem. Soc. 2020, 142, 18109; c) Mateo L. M. et al. Chem. Sci. 2021, 12, 247; d) Sun Q. et al. Angew. Chem. Int. Ed. 2021, 60, 16208; e) Sun, Q. et al. Adv. Sci. 2022, 9, 2105906; f) M. Tenorio, et al. Angew. Chem. Int. Ed. 2025, 64, e202420572.

 

To get an assistance certificate for this seminar, please, register here: https://docs.google.com/forms/d/e/1FAIpQLSdB-0YxKRrM-15cBS_ex8peGOR2GhSCu_wUG64y_1bccYAJnQ/viewform?usp=header