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Interplay of Anion-π+ and π+-π+ Interactions in Novel Pyrido[2,1-a]isoquinolinium-Based AIEgens - Substituent- and Counterion-Dependent Fluorescence Modulation and Applications in Live Cell Mitochondrial Imaging** |
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| Authors: | Dr Ravindra D Mule Rupam Roy Koushik Mandal Dr Deepak Chopra Tanoy Dutta Shashank P Sancheti Dr Popat S Shinde Dr Somsuvra Banerjee Dr Apurba Lal Koner Rohit Bhowal Dr Beeran Senthilkumar Dr Nitin T Patil |
| Institution: | 1. Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008 India
Academy of Scientific and Innovative Research, Ghaziabad, 201 002 India These authors contributed equally to this work.;2. Bionanotechnology Laboratory, Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, 462 066 India These authors contributed equally to this work.;3. Crystallography and Crystal Chemistry Laboratory, Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, 462 066 India;4. Bionanotechnology Laboratory, Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, 462 066 India;5. Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, 462 066 India;6. Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008 India Academy of Scientific and Innovative Research, Ghaziabad, 201 002 India;7. Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008 India |
| Abstract: | Recently, the concept of anion-π+ interactions has witnessed unique applications in the field of AIEgen development. In this contribution, we disclose a consolidated study of a library of N-doped ionic AIEgens accessed through silver-mediated cyclization of pyridino-alkynes. A thorough photophysical, computational and crystallographic study has been conducted to rationalize the observed substituent- and counterion-dependent fluorescence properties of these luminogens. We further elucidate the prominent role of anion-π+ interactions, π+-π+ interactions and other non-covalent interactions, in inhibiting the undesired ACQ effect. Finally, we have also demonstrated the application of selected AIEgens for imaging of mitochondria in live cells. |
| Keywords: | AIEgens anion-π+ crystal structure mitochondrial imaging pyrido[2 1-a]isoquinolinium |