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• W2043282620 abstract "Abstract Bis‐TMS protected C , C ‐diacetylenic phosphaalkene (A 2 PA) 1 (Mes*PC(C≡CTMS) 2 ; Mes*=2,4,6‐ t Bu 3 Ph) has been used as a building block for the construction of butadiyne‐expanded dendralene fragments in which phosphaalkenes feature as exotopic double bonds. Treatment of 1 with CuCl gives rise to a Cu I acetylide that is selectively formed at the acetylene trans to the Mes* group. The cis ‐TMS‐acetylene engages in similar chemistry, albeit at higher temperatures and longer reaction times. The differentiation between the two acetylene termini of 1 allows for the controlled synthesis of the title compounds by a variety of different Cu‐ and Pd‐catalyzed oxidative acetylene homo‐ and heterocoupling protocols. Crystallographic characterization of A 2 PA 1 and dimeric Mes*PC(C≡CR 1 )C 4 (R 2 C≡C)CPMes* ( 3 b , R 1 =R 2 =Ph; 6 , R 1 =R 2 =TMS), and 10 (R 1 =R 2 =C≡CPh) verifies that the stereochemistry across the PC bond is conserved during the coupling reactions, whereas spectroscopic evidence reveals cis / trans isomerization in an iodo‐substituted A 2 PA intermediate 4 (Mes*PC(C≡CTMS)(C≡CI). UV/Vis spectroscopic and electrochemical studies reveal that efficient π conjugation operates through the entire acetylenic phosphaalkene framework, even in the cross‐conjugated dimeric structures. The P centers contribute considerably to the frontier molecular orbitals of the compounds, thereby leading to smaller HOMO–LUMO gaps than in all‐carbon‐based congeners. Phenyl‐ and/or ethynylphenyl substituents at the A 2 PA framework influence the HOMO and LUMO to a varying degree depending on their relationship to the Mes* group, thus enabling a fine‐tuning of the frontier molecular orbitals of the compounds." @default.
• W2043282620 created "2016-06-24" @default.
• W2043282620 creator A5045357913 @default.
• W2043282620 creator A5048735875 @default.
• W2043282620 date "2011-09-14" @default.
• W2043282620 modified "2023-10-18" @default.
• W2043282620 title "Acetylene-Expanded Dendralene Segments with Exotopic Phosphaalkene Units" @default.
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• W2043282620 doi "https://doi.org/10.1002/chem.201101358" @default.
• W2043282620 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/21915927" @default.
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