Synthesis and Optical Properties of Unsymmetrically Substituted Triarylamine Hexaazatrinaphthalenes. Issue 17 (3rd May 2017)

• Record Type: Journal Article
• Authors: Larsen, Christopher B.; Barnsley, Jonathan E.; van der Salm, Holly; Fraser, Michael G.; Lucas, Nigel T.; Gordon, Keith C.
• Is Part Of: European journal of organic chemistry. Issue 17(2017)
• Page Start: 2432
• Page End: 2440
• Publication Date: 2017-05-03
• Subjects: Nitrogen heterocycles -- Donor–acceptor systems -- Raman spectroscopy -- Density functional calculations -- Photophysics; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700251
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : We report herein the synthesis and optical properties of unsymmetrically substituted hexaazatrinaphthalene (HATN) systems, and the influence of donor additivity on the electronic properties of the material. The hexaazatrinaphthalenes have been studied by means of electrochemical, electronic absorption and emission, FT Raman and resonance Raman methodologies coupled with DFT calculations. The optical spectra are dominated by low‐energy charge‐transfer states, which show a redshift of excitation energy of around 0.1 eV and an increase in ε of around 125 % as the number of donors is increased. The emission spectra exhibit significant solvatochromism, with Lippert–Mataga analysis yielding Δ µ values between 34 and 60 D. Abstract : Unsymmetrically substituted electron donor–acceptor hexaazatrinaphthalenes, prepared by a modular synthesis, demonstrate the effect of donor additivity on the electronic properties of the material.