| Autor: |
Jia Hong-Peng, Ding Jie, Ran Ying-Fen, Liu Shi-Xia, Blum Carmen, Petkova Irina, Hauser Andreas, Decurtins Silvio |
| Rok vydání: |
2011 |
| Zdroj: |
CHEMISTRY-AN ASIAN JOURNAL |
| DOI: |
10.1002/asia.201100515 |
| Popis: |
An efficient synthetic approach to a symmetrically functionalized tetrathiafulvalene (TTF) derivative with two diamine moieties 2 [56 diamino 47 bis(4 pentylphenoxy) 13 benzodithiol 2 ylidene] 47 bis(4 pentylphenoxy) 13 benzodithiole 56 diamine (2) is reported. The subsequent Schiff base reactions of 2 afford large p conjugated multiple donor–acceptor (D–A) arrays for example the triad 2 [49 bis(4 pentylphenoxy) 13 dithiolo[45 g]quinoxalin 2 ylidene] 49 bis(4 pentylphenoxy) 13 dithiolo[45 g]quinoxaline (8) and the corresponding tetrabenz[bcefhiuv]ovalene fused pentad 1 in good yields and high purity. The novel redox active nanographene 1 is so far the largest known TTF functionalized polycyclic aromatic hydrocarbon (PAH) with a well resolved 1H NMR spectrum. The electrochemically highly amphoteric pentad 1 and triad 8 exhibit various electronically excited charge transfer states in different oxidation states thus leading to intense optical intramolecular charge transfer (ICT) absorbances over a wide spectral range. The chemical and electrochemical oxidations of 1 result in an unprecedented TTF·+ radical cation dimerization thereby leading to the formation of [1·+]2 at room temperature in solution due to the stabilizing effect which arises from strong p–p interactions. Moreover ICT fluorescence is observed with large solvent dependent Stokes shifts and quantum efficiencies of 0.05 for 1 and 0.035 for 8 in dichloromethane. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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