Intramolecular Direct Arylation Enables Access to Diverse Photophysical Properties for π‐Expanded 1,4‐Dihydropyrrolo[3,2‐ b ]pyrroles
Abstract
Dyes incorporating 1,4-dihydropyrrolo [ 3,2-b ]pyrrole (DHPP) units are attractive platforms for organic optoelectronics because of their tunable electronic structures and intense fluorescence. Herein, we report a modular synthetic route to a diverse family of π-expanded DHPPs. The approach relies on double intramolecular direct arylation. This strategy provides efficient access to structurally complex dyes, including helically twisted and highly fused π-systems containing up to 20 conjugated aromatic rings and a unique combination of optical properties. Several of the obtained dyes display pronounced solvatochromism, red emission, and circularly polarized luminescence (CPL). In particular, chiral resolution of a helicene-type derivative enabled detailed chiroptical studies and revealed configurationally stable enantiomers with a good luminescence dissymmetry factor. A combination of experimental and computational analyses provided insight into the structure-property relationships governing their photophysical behavior, with particular emphasis on molecular symmetry and the substituent-dependent influence of nitro groups.
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BibTeX
@article{kusy2026intramolecular,
title = {{Intramolecular Direct Arylation Enables Access to Diverse Photophysical Properties for π‐Expanded 1,4‐Dihydropyrrolo[3,2‐ b ]pyrroles}},
author = {Damian Kusy and Krzysztof Górski and Carmelo Naim and Francesco Bertocchi and Nicolas Vanthuyne and Krzysztof Noworyta and Bartosz Szymański and Radosław Kamiński and Francesca Terenziani and Denis Jacquemin and Daniel T Gryko},
journal = {Advanced Optical Materials},
year = {2026},
month = nov,
doi = {10.1002/adom.71894},
url = {https://nantes-universite.hal.science/hal-05853516v1},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Intramolecular Direct Arylation Enables Access to Diverse Photophysical Properties for π‐Expanded 1,4‐Dihydropyrrolo[3,2‐ b ]pyrroles
AU - Damian Kusy
AU - Krzysztof Górski
AU - Carmelo Naim
AU - Francesco Bertocchi
AU - Nicolas Vanthuyne
AU - Krzysztof Noworyta
AU - Bartosz Szymański
AU - Radosław Kamiński
AU - Francesca Terenziani
AU - Denis Jacquemin
AU - Daniel T Gryko
PY - 2026
DA - 2026/11/05
JO - Advanced Optical Materials
DO - 10.1002/adom.71894
UR - https://nantes-universite.hal.science/hal-05853516v1
AB - Dyes incorporating 1,4-dihydropyrrolo [ 3,2-b ]pyrrole (DHPP) units are attractive platforms for organic optoelectronics because of their tunable electronic structures and intense fluorescence. Herein, we report a modular synthetic route to a diverse family of π-expanded DHPPs. The approach relies on double intramolecular direct arylation. This strategy provides efficient access to structurally complex dyes, including helically twisted and highly fused π-systems containing up to 20 conjugated aromatic rings and a unique combination of optical properties. Several of the obtained dyes display pronounced solvatochromism, red emission, and circularly polarized luminescence (CPL). In particular, chiral resolution of a helicene-type derivative enabled detailed chiroptical studies and revealed configurationally stable enantiomers with a good luminescence dissymmetry factor. A combination of experimental and computational analyses provided insight into the structure-property relationships governing their photophysical behavior, with particular emphasis on molecular symmetry and the substituent-dependent influence of nitro groups.
SN - 2195-1071
ER -