推拉式茚衍生物的全色荧光溶色性

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2025-02-14 DOI:10.1002/ejoc.202401471
Wakana Kanezaki, Ryutaro Ishikawa, Hayato Tsuji
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Full‐color Fluorescence Solvatochromism of Push‐pull Type Indenoindene Derivatives
Full‐color fluorescence solvatochromism was demonstrated using two carbon‐bridged oligo(phenylenevinylene) (COPV) derivatives Ph2N‐COPV1(Bu)‐COCH3 and [Ph2N‐COPV1(Bu)]2CO with a push–pull system, where the donor and acceptor moieties are diphenylamino and a carbonyl group, respectively. In non‐polar cyclohexane, the molecules exhibited blue photoluminescence (λPL = 443 and 464 nm) with a locally excited character, while in polar solvents, a charge‐transfer character emerged. In methanol, red emission was observed (λPL = 602 and 572 nm). The difference in luminescence maxima between cyclohexane and methanol corresponds to 0.74 and 0.59 eV for Ph2N‐COPV1(Bu)‐COCH3 and [Ph2N‐COPV1(Bu)]2CO, respectively, which are larger than those of previously reported push–pull systems. The photoluminescence quantum yields of Ph2N‐COPV1(Bu)‐COCH3 in aprotic solvents were 0.90 and higher regardless of solvent polarity, while they decreased in protic solvents. The molecules also display high extinction coefficients of up to 2.8 x 104 and 6.4 x 104 M⁻¹cm⁻¹. These data demonstrate the effectiveness of the use of structurally rigid planar COPV framework. Furthermore, [Ph2N‐COPV1(Bu)]2CO showed significant responses to water content in tetrahydrofuran‐water mixed solvents, which highlights its potential for sensing applications.
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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