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Dipyrrolonaphthyridinedione – (still) a mysterious cross-conjugated chromophore
(Royal Society of Chemistry, 2023)
Dipyrrolonaphthyridinediones (DPNDs) entered the chemical world in 2016. This cross-conjugated donor–acceptor skeleton can be prepared in two steps from commercially available reagents in overall yieldz15–20% (5 mmol scale). ...
Unprecedented 1,2-Aryl Shift Accompanying Double Alkyne Benzannulation
(Wiley, 2023)
The tandem intramolecular hydroarylation of alkynes accompanied by a 1,2-aryl shift is described. Harnessing the unique electron-rich character of 1,4-dihydropyrrolo[3,2-b]pyrrole scaffold, we demonstrate that the ...
Novel Method for the Synthesis of Merocyanines: New Photophysical Possibilities for a Known Class of Fluorophores
(Wiley, 2023)
A 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 ...
Saddle-shaped aza-nanographene with multiple odd-membered rings
(Royal Society of Chemistry, 2023)
A saddle-shaped aza-nanographene containing a central 1,4-dihydropyrrolo[3,2-b]pyrrole (DHPP) has been prepared via a rationally designed four-step synthetic pathway encompassing intramolecular direct arylation, the Scholl ...
Green-Emitting 4,5-Diaminonaphthalimides in Activity-Based Probes for the Detection of Thrombin
(American Chemical Society, 2022)
The natures of electron-donating groups as well as the bridge between them determine the fate of substituted 1,8-naphthalimide molecules in the excited state. An activity-based probe constructed from a selective peptide ...
Conformation of the Ester Group Governs the Photophysics of Highly Polarized Benzo[g]coumarins
(American Chemical Society, 2023)
Photosensitizers that display “unusual” emission from upper electronically excited states offer possibilities for initiating higher-energy processes than what the governing Kasha’s rule postulates. Achieving conditions for ...
From 2,5-Diformyl-1,4-dihydropyrrolo[3,2-b]pyrroles to Quadrupolar, Centrosymmetric Two-Photon-Absorbing A–D–A Dyes
(American Chemical Society, 2022-03-28)
An original approach has been developed for the insertion of formyl substituents at positions 2 and 5 of 1,4-dihydropyrrolo[3,2-b]pyrroles by conversion of thiazol-2-yl sub stituents. The synthetic utility of these formyl ...
Multifunctional Heteropentalenes: From Synthesis to Optoelectronic Applications
(American Chemical Society, 2022)
In the broad family of heteropentalenes, the combination of two five-membered heterocyclic rings fused in the [3,2-b] mode has attracted the most significant attention. The relatively straightforward access to these ...
Polarized, V-Shaped, and Conjoined Biscoumarins: From Lack of Dipole Moment Alignment to High Brightness
(American Chemical Society, 2022)
Eleven conjoined coumarins possessing a chromeno[3,4-c]chromene-6,7-dione skeleton have been synthesized via the reaction of electron-rich phenols with esters of coumarin-3-carboxylic acids, catalyzed by either Lewis acids ...
On-off-on Control of Molecular Inversion Symmetry via Multi-stage Protonation: Elucidating Vibronic Laporte Rule
(Wiley, 2022)
The Laporte rule dictates that one- and two-photon absorption spectra of inversion-symmetric molecules should display alternatively forbidden electronic transitions; however, for organic fluorophores, drawing clear distinction ...