[HTML][HTML] The shape of porphyrins

CJ Kingsbury, MO Senge - Coordination Chemistry Reviews, 2021 - Elsevier
Porphyrin molecules are a widely exploited biochemical moiety, with uses in medicinal
chemistry, sensing and materials science. The shape of porphyrins, as an aromatic unit, is …

Nonplanar porphyrins: synthesis, properties, and unique functionalities

T Ishizuka, N Grover, CJ Kingsbury, H Kotani… - Chemical Society …, 2022 - pubs.rsc.org
Porphyrins are variously substituted tetrapyrrolic macrocycles, with wide-ranging biological
and chemical applications derived from metal chelation in the core and the 18π aromatic …

Unraveling the pivotal role of atropisomerism for cellular internalization

C Donohoe, FA Schaberle… - Journal of the …, 2022 - ACS Publications
The intrinsic challenge of large molecules to cross the cell membrane and reach intracellular
targets is a major obstacle for the development of new medicines. We report how rotation …

Porphyrin Atropisomerism as a Molecular Engineering Tool in Medicinal Chemistry, Molecular Recognition, Supramolecular Assembly, and Catalysis

S Maguire, G Strachan, K Norvaiša… - … A European Journal, 2024 - Wiley Online Library
Porphyrin atropisomerism, which arises from restricted σ‐bond rotation between the
macrocycle and a sufficiently bulky substituent, was identified in 1969 by Gottwald and …

A nonneglectable stereochemical factor in drug development: Atropisomerism

YD Yang, BB Yang, L Li - Chirality, 2022 - Wiley Online Library
Chirality is one of the key factors affecting the medicinal efficacy of compounds. In addition to
central chirality, sterically hindered chiral axes commonly appear in drugs and the resulting …

In Situ Probe Supramolecular Self-Assembly Dynamics and Chirality Transfer Mechanism at Air–Water Interface

Y Zhang, C Yu, L Han, M Liu, Y Guo… - The Journal of Physical …, 2022 - ACS Publications
The study of supramolecular self-assembly dynamics and the chirality transfer mechanism is
of importance to the rational design of potentially functional chiral supramolecular materials …

Supramolecular Chirogenesis in a Sterically Hindered Porphyrin: A Critical Theoretical Analysis

I Osadchuk, HE Luts, K Norvaiša… - … A European Journal, 2023 - Wiley Online Library
The determination of molecular stereochemistry and absolute configuration is an important
part of modern chemistry, pharmacology, and biology. Electronic circular dichroism (ECD) …

Molecular Symmetry and Art: Visualizing the Near‐Symmetry of Molecules in Piet Mondrian's De Stijl

CJ Kingsbury, MO Senge - Angewandte Chemie International …, 2024 - Wiley Online Library
Symmetry and shape are essential aspects of molecular structure and how we interpret
molecules and their properties. We, as chemists, are comfortable with pictorial …

Steric repulsion induced conformational switch in supramolecular structures

K Norvaiša, S Maguire, C Donohoe… - … A European Journal, 2022 - Wiley Online Library
Inspired by the rigidified architecture of 'picket‐fence'systems, we propose a strategy utilizing
strain to impose intramolecular tension in already peripherally overcrowded structures …

Atropisomeric conjugated diimides: a class of thermally responsive organic semiconductors

C Ge, W Zhang, WL Tan, CR McNeill… - ACS Materials …, 2022 - ACS Publications
Atropisomerism has been studied in many research fields; however, it is rarely studied in
organic semiconductors. In this work, we report a series of room-temperature-stable …