1,3‐Diynes as Precursors for the Synthesis of Triazene‐ and Diethylaniline‐Bearing Push‐Pull NLOphores

Date

2024-02-01

Author

Inyurt, Fevzi Can
Dengiz, Çağatay

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Withinthe scopeof this study,a total of eight new NLOphoresof the D-π-A-π-Dtype have been synthesized.This was achievedby applyingclick-type[2+2] cycloaddition-retroelectrocycliza-tion reactionsof unsymmetrical1,3-diyneswith well-knownelectron-deficientalkenes,TCNE,and TCNQ.Furthermore,essentialinsightsinto the opticalpropertiesof the synthesizedNLOphoreswere obtainedfrom comparisonswith four modelcompoundssynthesizedseparatelywithinthis study.Thethermalstabilityof the NLOphoreswas assessedthroughthermalgravimetricanalysis(TGA).NLOphoressynthesizedusing two distinctelectron-deficientalkenesexhibitlow energyabsorptionbandscoveringmost of the visibleregionwithλmaxvaluesrangingfrom 466 nm to 723 nm. Theoreticalstudies,includingtime–dependentdensityfunctionaltheory(TD-DFT)investigations,frontierorbitalvisualizations,and electrostaticpotentialmaps,have been utilizedto furtherinvestigatetheintramolecularchargetransferpropertiesof chromophores.TheNLO responsesof the chromophoreswere determinedthroughDFT calculations.It is worthnotingthat the averagepolar-izabilityand first hyperpolarizabilityvalues(α(tot)=106.392–159.709×10

URI

https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/slct.202304394
https://hdl.handle.net/11511/108634

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Department of Chemistry, Article