Affiliation:
1. Department of Chemistry, Life Sciences and Environmental Sustainability University of Parma Parco Area delle Scienze 17/a 43124 Parma Italy
2. Institute of Organic Chemistry Polish Academy of Sciences Warsaw Poland
3. Faculty of Chemistry University of Warsaw Żwirki i Wigury 101 02-089 Warsaw Poland
Abstract
AbstractA new, transformative method for the preparation of rhodols and other merocyanines from readily available tetrafluorohydroxybenzaldehyde and aminophenols has been developed. It is now possible to prepare merocyanines bearing three fluorine atoms and additional conjugated rings, and the whole one‐pot process occurs under neutral, mild conditions. Three heretofore unknown merocyanine‐based architectures were prepared using this strategy from aminonaphthols and 4‐hydroxycoumarins. The ability to change the structure of original rhodol chromophore into π‐expanded merocyanines translates to a comprehensive method for the modulation of photophysical properties, such as shifting the absorption and emission bands across almost the entire visible spectrum, reaching a huge Stokes shift i. e. 4800 cm−1, brightness approximately 80.000 M−1 cm−1, two‐photon absorption cross‐section above 150 GM and switching‐on/off solvatofluorochromism. A detailed investigation allowed to rationalize the different spectroscopic behavior of rhodols and new merocyanines, addressing solvatochromism and two‐photon absorption.
Funder
Fundacja na rzecz Nauki Polskiej
H2020 Marie Skłodowska-Curie Actions
Ministero dell’Istruzione, dell’Università e della Ricerca
Subject
General Chemistry,Catalysis,Organic Chemistry