Mapping the influence of ligand electronics on the spectroscopic and 1O 2 sensitization characteristics of Pd( ii ) biladiene complexes bearing phenyl–alkynyl groups at the 2- and 18-positions

Martin, Maxwell I.; Pham, Trong-Nhan; Ward, Kaytlin N.; Rice, Anthony T.; Hertler, Phoebe R.; Yap, Glenn P.  A.; Gilmartin, Philip H.; Rosenthal, Joel

doi:10.1039/d3dt00691c

Mapping the influence of ligand electronics on the spectroscopic and ¹O ₂ sensitization characteristics of Pd( ii ) biladiene complexes bearing phenyl–alkynyl groups at the 2- and 18-positions

Journal Article · Thu May 18 00:00:00 EDT 2023 · Dalton Transactions

DOI:https://doi.org/10.1039/d3dt00691c· OSTI ID:2422516

Martin, Maxwell I. ^[1]; ^[2]; Ward, Kaytlin N. ^[2]; Rice, Anthony T. ^[2]; Hertler, Phoebe R. ^[2]; ^[2]; Gilmartin, Philip H. ^[2]; ^[2]

Univ. of Delaware, Newark, DE (United States); OSTI
Univ. of Delaware, Newark, DE (United States)

Photodynamic therapy (PDT) is a promising treatment for certain cancers that proceeds via sensitization of ground state ³O₂ to generate reactive ¹O₂. Classic macrocyclic tetrapyrrole ligand scaffolds, such as porphyrins and phthalocyanines, have been studied in detail for their ¹O₂ photosensitization capabilities. Despite their compelling photophysics, these systems have been limited in PDT applications because of adverse biological side effects. Conversely, the development of non-traditional oligotetrapyrrole ligands metalated with palladium (Pd[DMBil1]) have established new candidates for PDT that display excellent biocompatibility. Herein, the synthesis, electrochemical, and photophysical characterization of a new family of 2,18-bis(phenylalkynyl)-substituted Pd^II 10,10-dimethyl-5,15-bis(pentafluorophenyl)-biladiene (Pd[DMBil2-R]) complexes is presented. These second generation biladienes feature extended conjugation relative to previously characterized Pd^II biladiene scaffolds (Pd[DMBil1]). We show that these new derivatives can be prepared in good yield and, that the electronic nature of the phenylalkynyl appendages dramatically influence the Pd^II biladiene photophysics. Extending the conjugation of the Pd[DMBil1] core through installation of phenylacetylene resulted in a ~75 nm red-shift of the biladiene absorption spectrum into the phototherapeutic window (600–900 nm), while maintaining the Pd^II biladiene's steady-state spectroscopic ¹O₂ sensitization characteristics. Varying the electronics of the phenylalkyne groups via installation of electron donating or withdrawing groups dramatically influences the steady-state spectroscopic and photophysical properties of the resulting Pd[DMBil2-R] family of complexes. The most electron rich variants (Pd[DMBil2-N(CH3)2]) can absorb light as far red as ~700 nm but suffer from significantly reduced ability to sensitize formation of ¹O₂. By contrast, Pd[DMBil2-R] derivatives bearing electron withdrawing functionalities (Pd[DMBil2-CN] and Pd[DMBil2-CF3]) display ¹O₂ quantum yields above 90%. The collection of results we report suggest that excited state charge transfer from more electron-rich phenyl-alkyne appendages to the electron deficient biladiene core circumvents triplet sensitization. The spectral and redox properties, as well as the triplet sensitization efficiency of each Pd[DMBil2-R] derivative is considered in relation to the Hammett value (σp) for each biladiene's R-group. More broadly, the results reported in this study clearly demonstrate that biladiene redox properties, spectral properties, and photophysics can be perturbed greatly by relatively minor alterations to biladiene structure.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of California, Los Angeles, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0001234

OSTI ID:: 2422516

Alternate ID(s):: OSTI ID: 2505699
OSTI ID: 1974302

Journal Information:: Dalton Transactions, Journal Name: Dalton Transactions Journal Issue: 22 Vol. 52; ISSN 1477-9226; ISSN ICHBD9

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Mapping the influence of ligand electronics on the spectroscopic and ¹O ₂ sensitization characteristics of Pd( ii ) biladiene complexes bearing phenyl–alkynyl groups at the 2- and 18-positions