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Cover Picture: meso ‐ N ‐Pyrrole as a Versatile Substituent Influencing the Optical Properties of Porphyrin (Chem. Asian J. 23/2016)
Author(s) -
Hurej Karolina,
Stawski Wojciech,
LatosGrażyński Lechosław,
Pawlicki Miłosz
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601408
Subject(s) - pyrrole , deprotonation , porphyrin , pyridine , substituent , chemistry , delocalized electron , photochemistry , indolizine , medicinal chemistry , organic chemistry , ion
A pyrrole unit attached directly to the meso ‐position changes the optical behavior of porphyrin after efficient condensation that extends the π‐delocalization over the newly formed indolizine‐3‐one unit. The strongly affected electronic properties are further modified by a lactam opening reaction. The formed pyridine‐like unit exposes the nitrogen and forms a trigger, significantly modifying both absorbance and emission after a fundamental initiation (i.e., deprotonation). Importantly, the pyridine‐containing motif enhances the bathochromically shifted emission while the deprotonated form was obtained, opening the possibility of using such compounds, for instance, as fluorogenic sensors. More information can be found in the Communication by Miłosz Pawlicki and co‐workers on page 3329 in Issue 23, 2016 (DOI: 10.1002/asia.201601210).