Phosphorescence Induction by Host-Guest Complexation with Cyclodextrins - The Role of Regioisomerism and Affinity

被引：9

作者：

Hayduk, Matthias ^{[1
,2
]}

Schaller, Torsten ^{[1
,2
]}

Niemeyer, Felix C. ^{[1
,2
]}

Rudolph, Kevin ^{[1
,2
]}

Clever, Guido H. ^{[3
]}

Rizzo, Fabio ^{[4
,5
]}

Voskuhl, Jens ^{[1
,2
]}

机构：

[1] Univ Duisburg Essen, Fac Chem Organ Chem, ZMB, Univ Str 7, D-45141 Essen, Germany

[2] Univ Duisburg Essen, CENIDE, Univ Str 7, D-45141 Essen, Germany

[3] Tech Univ Dortmund, Fak Chem & Chem Biol, Otto Hahn Str 6, D-44227 Dortmund, Germany

[4] Natl Res Council CNR, Inst Chem Sci & Technol G Natta SCITEC, Via G Fantoli 16-15, I-20138 Milan, Italy

[5] Westfalische Wilhelms Univ Munster, Ctr Soft Nanosci SoN, Busso Peus Str 10, D-48149 Munster, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2022年 / 28卷 / 51期

关键词：

cyclodextrins; host-guest systems; isothermal titration calorimetry; room temperature phosphorescence; supramolecular chemistry; ROOM-TEMPERATURE PHOSPHORESCENCE; AGGREGATION-INDUCED EMISSION; BETA-CYCLODEXTRIN; RECOGNITION; TETRAPHENYLETHENE; CUCURBITURILS; NANODIAMONDS; ENHANCEMENT; INCLUSION; CHEMISTRY;

D O I：

10.1002/chem.202201081

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present an in-depth investigation of cyclodextrin complexes with guest compounds featuring complexation-induced room temperature phosphorescence (RTP) in aqueous solution. Very interestingly, only the complexed regioisomers bearing lateral substituents on meta-position show RTP, whereas the stronger host-guest systems with para-substituted dyes show no RTP features. The reported systems were investigated regarding their complexation behavior in water using isothermal titration calorimetry and mass spectrometry. In the case of gamma-CD very strong 1 : 1 inclusion complexes (K-a up to 5.13x10(5) M-1) were unexpectedly observed. It was found that not only a strong binding to the cyclodextrin cavity is needed to restrict motion, inducing the emission, but also the conformation inside the cavity plays a pivotal role - as supported by an extensive NMR study and MD simulations.

引用

页数：11

共 73 条

[1] Structure and luminescence properties of supramolecular polymers of amphiphilic aromatic thioether-peptide conjugates in water [J].