Benzo[c,d]indole‐Containing Aza‐BODIPY Dyes: Asymmetrization‐Induced Solid‐State Emission and Aggregation‐Induced Emission Enhancement as New Properties of a Well‐Known Chromophore |
| |
| Authors: | Prof?Dr Soji Shimizu Ai Murayama Takuya Haruyama Taku Iino Dr Shigeki Mori Prof?Dr Hiroyuki Furuta Prof?Dr Nagao Kobayashi |
| |
| Affiliation: | 1. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819‐0395 (Japan);2. Center for Molecular Systems (CMS), Kyushu University, Fukuoka 819‐0395 (Japan);3. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan);4. Division of Material Science, Advanced Research Support Center, Ehime University, Matsuyama 790‐8577 (Japan);5. Faculty of Textile Science and Technology, Shinshu University, Ueda 386‐8567 (Japan) |
| |
| Abstract: | A series of symmetric and asymmetric benzoc,d]indole‐containing aza boron dipyrromethene (aza‐BODIPY) compounds was synthesized by a titanium tetrachloride‐mediated Schiff‐base formation reaction of commercially available benzoc,d]indole‐2(1H)‐one and heteroaromatic amines. These aza‐BODIPY analogues show different electronic structures from those of regular aza‐BODIPYs, with hypsochromic shifts of the main absorption compared to their BODIPY counterparts. In addition to the intense fluorescence in solution, asymmetric compounds exhibited solid‐state fluorescence due to significant contribution of the vibronic bands to both absorption and fluorescence as well as reduced fluorescence quenching in the aggregates. Finally, aggregation‐induced emission enhancement, which is rare in BODIPY chromophores, was achieved by introducing a nonconjugated moiety into the core structure. |
| |
| Keywords: | aggregation dyes/pigments fluorescence nitrogen heterocycles solid‐state emission |
|
|
