First-Principles Analysis of Protonation-Induced Electronic Effects in Tetrakis(p‑aminophenyl)porphyrin (TAPP)

in: Journal of Physical Chemistry A (2026)
Roy, Arghyadeb; Elmanova, Anna; Jayan, Sujith; Hupfer, Maximilian L.; Martínez, Todd J.; Gryko, Daniel T.; Presselt, Martin
The optical response of pH-sensitive porphyrins depends critically on the protonation site, not merely on the total charge accumulated. Using first-principles linear-response theory, we systematically map all symmetry-distinct protonation states of tetrakis( p -aminophenyl)porphyrin (TAPP), from neutral to fully protonated (+6), revealing that peripheral and core protonation produce fundamentally different photophysical outcomes. Peripheral protonation progressively attenuates Q-band intensity while leaving the macrocyclic core electronically intact, whereas core protonation drives conformer convergence, pronounced Q-band red-shifting, intensification, and merging of split-transition upon diprotonation. Q-band oscillator strength thus evolves nonmonotonically across protonation topologies─enhanced by core protonation through orbital mixing and suppressed by peripheral protonation through donor decoupling. At intermediate mixed protonation states (+4/+5), remaining unprotonated aminophenyl groups act as donors in aminophenyl-to-macrocycle charge transfer (CT) excitations, identified through charge-density difference (CDD) analysis. Core protonation additionally widens the singlet–triplet gap (Δ E ST ) relative to peripheral protonation, with implications for intersystem crossing (ISC) and triplet-state engineering. Together, these results establish protonation topology as a molecular design parameter for controlling absorption, CT character, and excited-state properties in pH-responsive porphyrin systems.

Third party cookies & scripts

This site uses cookies. For optimal performance, smooth social media and promotional use, it is recommended that you agree to third party cookies and scripts. This may involve sharing information about your use of the third-party social media, advertising and analytics website.
For more information, see privacy policy and imprint.
Which cookies & scripts and the associated processing of your personal data do you agree with?

You can change your preferences anytime by visiting privacy policy.