Bridged Indolizine‐Naphthyridines: Synthesis and Initial Photophysical Characterization

In this work, we synthesized a new series of hybrid compounds combining an indolizine unit and a 1,8‐naphthyridine moiety through an optimized Friedländer reaction. These systems were designed to evaluate how electronic effects and conformational rigidity influence their photophysical properties. The compounds were obtained in up to 95% yield and in short reaction time. Among the synthesized derivatives, compounds 3a and 3j were selected for an initial photophysical analysis. Both exhibited solvent‐dependent absorption and emission behavior, with 3a showing the highest emission quantum yield. The formation of a six‐membered ring connecting both heterocycles increases molecular rigidity, restricts bond rotation, and facilitates intramolecular charge transfer. The promising initial results pave the way for future investigations into the potential applications of these novel indolizine‐[1,8]‐naphthyridine hybrids in fluorescence‐based materials.

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Journal
European Journal of Organic Chemistry
Published
2026-06-30
DOI
https://doi.org/10.1002/ejoc.70643
Primary Topic
Synthesis and Reactivity of Heterocycles
Type
article
Field-Weighted Citation Impact
0.00

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article

Bridged Indolizine‐Naphthyridines: Synthesis and Initial Photophysical Characterization

Ana Julia Senna, Manoel T. Rodrigues, Fernando Coelho, Brenno A. D. Neto et al.
European Journal of Organic Chemistry
Synthesis and Reactivity of Heterocycles
article

Bridged Indolizine‐Naphthyridines: Synthesis and Initial Photophysical Characterization

Ana Julia Senna, Manoel T. Rodrigues, Fernando Coelho, Brenno A. D. Neto, Patrícia M. Alves, Thaynan A. B. Chagas, Raíssa K. C. de Paiva
article en

Abstract

In this work, we synthesized a new series of hybrid compounds combining an indolizine unit and a 1,8‐naphthyridine moiety through an optimized Friedländer reaction. These systems were designed to evaluate how electronic effects and conformational rigidity influence their photophysical properties. The compounds were obtained in up to 95% yield and in short reaction time. Among the synthesized derivatives, compounds 3a and 3j were selected for an initial photophysical analysis. Both exhibited solvent‐dependent absorption and emission behavior, with 3a showing the highest emission quantum yield. The formation of a six‐membered ring connecting both heterocycles increases molecular rigidity, restricts bond rotation, and facilitates intramolecular charge transfer. The promising initial results pave the way for future investigations into the potential applications of these novel indolizine‐[1,8]‐naphthyridine hybrids in fluorescence‐based materials.

European Journal of Organic Chemistry
Universidade Estadual de Campinas (UNICAMP) (BR), Universidade Estadual de Goiás (BR), Institute of Physics (AZ)
Fundação de Amparo à Pesquisa do Estado de São Paulo, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico
Openalex Percentile: Top 14%
Synthesis and Reactivity of Heterocycles
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