1,6-Diazapyrene: A Novel, Well-Defined, Small-Size Prototype System for Nitrogen-Containing PAHs
| Title: | 1,6-Diazapyrene: A Novel, Well-Defined, Small-Size Prototype System for Nitrogen-Containing PAHs |
|---|---|
| Authors: | Indranil Bhattacharjee; Liangxuan Wang; Nerea Gonzalez-Sanchis; Begoña Milián-Medina; Rafael Ballesteros; Reinhold Wannemacher; Rafael Ballesteros-Garrido; Johannes Gierschner |
| Publication Year: | 2025 |
| Subject Terms: | Biochemistry; Medicine; Genetics; Immunology; Infectious Diseases; Plant Biology; Space Science; Biological Sciences not elsewhere classified; Chemical Sciences not elsewhere classified; td -) dft; size prototype system; polycyclic aromatic hydrocarbons; density functional theory; photochemical deactivation kinetics; employing optical spectroscopy; revealing extreme changes; defined prototype systems; photochemical properties; optical excitations; topology considerations; targeted design; substitution position; mo symmetry; known 2; highly relevant; high sensitivity; depth analysis |
| Description: | The quest for nitrogen-doped (N-doped) polycyclic aromatic hydrocarbons (PAHs) requires well-defined prototype systems to understand the relationship between the structure and the resulting photophysical and photochemical properties. To this end, a novel, simple, and small compound, 1,6-diazapyrene, was synthesized. In-depth analysis, employing optical spectroscopy and (time-dependent) density functional theory, (TD-)DFT, elucidates the optical excitations on the basis of MO symmetry, energy, and topology considerations; the study further unveils the photophysical and photochemical deactivation kinetics after photoexcitation, revealing extreme changes against pyrene as well as against the well-known 2,7-diazapyrene isomer. The high sensitivity of the aza-substitution position to generate such changes is considered as highly relevant for the targeted design of N-doped PAHs in general. |
| Document Type: | article in journal/newspaper |
| Language: | unknown |
| DOI: | 10.1021/acs.jpca.5c01474.s001 |
| Availability: | https://doi.org/10.1021/acs.jpca.5c01474.s001; https://figshare.com/articles/journal_contribution/1_6-Diazapyrene_A_Novel_Well-Defined_Small-Size_Prototype_System_for_Nitrogen-Containing_PAHs/29041672 |
| Rights: | CC BY-NC 4.0 |
| Accession Number: | edsbas.BAEA0838 |
| Database: | BASE |