A push-pull aromatic chromophore with a touch of merocyanine.
The solvatochromic behavior of N-(2,5-di-tert-butylphenyl)-9-pyrrolidinoperylene-3,4-dicarboximide () was investigated by measuring the excitation and emission spectra over a wide range of temperature in 2-methyltetrahydrofuran (MTHF). The temperature induced spectral changes can be compared with the changes caused by changing solvent polarity using different solvents at room temperature. In both cases a strong positive solvatochromism is observed both in absorption/excitation and in emission. The difference between excitation and emission energies decreases with increasing solvent polarity. The behavior of can be rationalized in terms of a change in electronic structure with solvent polarity. Although has the typical molecular structure of a push-pull substituted aromatic system, in which the solvatochromic shift in emission is normally larger than that in absorption, in its solvent-induced electronic structure change it resembles a merocyanine.
Zoon
Peter D
PD
University of Amsterdam, van 't Hoff Institute for Molecular Sciences, Nieuwe Achtergracht 129, 1018 WS, Amsterdam, The Netherlands.
Brouwer
Albert M
AM
D000042:Absorption; D005456:Fluorescent Dyes / Q000737:chemistry*; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry*; D011744:Pyrimidinones / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature
D005456:Fluorescent Dyes; C515943:N-(2,5-di-tert-butylphenyl)-9-piperidinoperylene-3,4-dicarboximide; D010880:Piperidines; D011744:Pyrimidinones; D012997:Solvents; C003954:merocyanine dye; D010569:Perylene