Carbamate‐Functionalized NLOphores via a Formal [2+2] Cycloaddition‐Retroelectrocyclization Strategy DOI Creative Commons
İpek Savaş, M. Çelik, Alberto Barsella

et al.

Chemistry - A European Journal, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

This study introduces a new donor group capable of activating click-type [2+2] cycloaddition-retroelectrocyclizations, generally known for their limited scope. Target chromophores were synthesized using isocyanate-free urethane synthesis. The developed synthetic method allows the tuning optical properties by modifying groups, acceptor units, and side chains. charge transfer (CT) bands exhibit λmax values ranging from 363 to 692 nm. CT observed have been supported solvatochromism protonation experiments. compounds positive solvatochromism. Due potential as NLOphore candidates, stability investigated both experimentally through TGA theoretically calculating parameters such frontier orbital energy differences, electronegativity, global hardness/softness. TD-DFT calculations used elucidate nature electronic transitions, revealing that correspond arising HOMO-to-LUMO excitations. NLO DFT methods EFISHG technique. Both results are shown be in agreement with HOMO-LUMO differences. experimental μβ selected molecules range 470×10-48 5400×10-48 esu.

Language: Английский

Synthesis and Optical Characterization of Hydrazone-Substituted Push–Pull-Type NLOphores DOI Creative Commons
Kübra Erden, Dilek Söyler, Alberto Barsella

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13192 - 13207

Published: Sept. 10, 2024

Two distinct families of NLOphores featuring hydrazone donors were synthesized using click-type [2 + 2] cycloaddition retroelectrocyclizations (CA-RE). Despite the limitations in substrate scope, it was shown for first time that hydrazone-activated alkynes could undergo reactions with TCNE/TCNQ. The electrochemical, photophysical, and second-order nonlinear optical (NLO) characteristics chromophores analyzed utilizing experimental computational approaches. Chromophores

Language: Английский

Citations

4
Carbamate‐Functionalized NLOphores via a Formal [2+2] Cycloaddition‐Retroelectrocyclization Strategy DOI Creative Commons
İpek Savaş, M. Çelik, Alberto Barsella

et al.

Chemistry - A European Journal, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

This study introduces a new donor group capable of activating click-type [2+2] cycloaddition-retroelectrocyclizations, generally known for their limited scope. Target chromophores were synthesized using isocyanate-free urethane synthesis. The developed synthetic method allows the tuning optical properties by modifying groups, acceptor units, and side chains. charge transfer (CT) bands exhibit λmax values ranging from 363 to 692 nm. CT observed have been supported solvatochromism protonation experiments. compounds positive solvatochromism. Due potential as NLOphore candidates, stability investigated both experimentally through TGA theoretically calculating parameters such frontier orbital energy differences, electronegativity, global hardness/softness. TD-DFT calculations used elucidate nature electronic transitions, revealing that correspond arising HOMO-to-LUMO excitations. NLO DFT methods EFISHG technique. Both results are shown be in agreement with HOMO-LUMO differences. experimental μβ selected molecules range 470×10-48 5400×10-48 esu.

Language: Английский

Citations

0