Texaphyrin Conjugates. Progress Towards Second Generation Diagnostic and Therapeutic Agents

Wei, W.; Fountain, Mark; Sessler, Jonathan L.; Magda, Darren; Wang, Zhong; Miller, Richard A.

doi:10.1007/1-4020-3687-6_25

Cited by 3 publications

(1 citation statement)

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“…lanthanides and actinides , and this feature is particularly appealing in the field of magnetic resonance imaging (MRI) and nuclear remediation technologies, respectively. Their large central cavities can also function as anion receptors; therefore, expanded analogues are pursued for anion sensing and transport. ,, Finally, expanded macrocycles possess extended conjugated π-systems that are associated to red-shifted absorptions in the visible region, and hence, they are potentially useful as therapeutic agents in photodynamic therapy (PDT) or radiotherapy as nonlinear optical materials, , and in optical limiting . All these incentives and others have motivated researchers to design and synthesize a large assortment of expanded porphyrinoids.…”

Section: Introductionmentioning

confidence: 99%

Scrutinizing the Chemical Nature and Photophysics of an Expanded Hemiporphyrazine: The Special Case of [30]Trithia-2,3,5,10,12,13,15,20,22,23,25,30-dodecaazahexaphyrin

et al. 2010

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Thirty π-electron-expanded hemiporphyrazines 1a-c have been prepared by crossover condensation reaction of 2,5-diamino-1,3,4-thiadiazole and the corresponding phthalonitrile (3) or diiminoisoindoline (4) derivatives. The expanded azaporphyrin hexamers have been unequivocally characterized by means of spectroscopic, crystallographic, and electrochemical techniques. Weak intramolecular hydrogen bonding imposes a planar conformation to macrocycles. However, the overall electronic delocalization is low, and the nature of the resulting [30]heteroannulene is nonaromatic, as confirmed by NMR studies, XR diffraction analysis, and calculation of the NICS(0) value. Studies on a wide range of physicochemical features including ground, excited, reduced, and oxidized states provide evidence for the wide applicability of these 30 π-electron-expanded hemiporphyrazines in processes involving electron transfer. A key asset of our work is the systematic development of spectroscopic and kinetic markers for the formation and decay of all of the aforementioned species. Thirty π-electron-expanded hemiporphyrazines evolve as broadly absorbing light harvesters with excited state energies of around 2.3 eV that are susceptible to facile one-electron reduction and one-electron oxidation reactions.

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