Like many other pigment classes, DPP pigments fluoresce in solution. The Stokes shifts are in the range of 10-15 nm and the fluorescence quantum yields ca. 60% [16]. In the solid state, some DPPs show a minor fluorescence. Through N substitution, both the solubility and the Stokes shift can be increased.
Some specific N-substituted DPP also show a strong solid-state fluorescence. One interesting case has been described by Langhals [17], where the DPP 23 can
crystallize in two different crystal modifications, one strongly fluorescing and the other showing only a very weak fluorescence. The two modifications showing different optical properties can be interconverted through a heating/crystallization process thus being principally interesting for information storage applications [18]. Another use as a light guide concentrator has been described [19].
As an alternative to N-alkylation or-arylation the formation of complexes, e. g., with Au, can also lead to highly soluble and strongly fluorescing DPP derivatives [20].
Further photophysical studies on fluorescing DPPs have been conducted by Johansson [21] including spectroscopic studies of a DPP in a lyotropic nematic liquid crystal and a comparison of the molecular symmetry of the ground state versus the first excited state.
Table 11.2 Absorptions and emissions of DPP [9, 17].
| DPP | R | R’ | k a kmax (absorption/nm) | k a kmax (fluoresence/nm) | фь (%) | 
| 2 | H | H | 496 | 509 | — | 
| 15 | 4-t-Bu | H | 502 | 513 | 63 | 
| 16 | 3,5-t-Bu | H | 500 | 513 | 63 | 
| 17 | 2-Me | H | 448 | 518 | 64 | 
| 18 | H | CH3 | 474 | 523 | 54 | 
| 19 | 4-t-Bu | CH3 | 485 | 528 | 53 | 
| 20 | 3,5-t-Bu | CH3 | 484 | 525 | 56 | 
| 21 | 2-Me | CH3 | 439 | 489 | 95 | 
| 22 | H | Ph | 484 | 520 (555sh) | 
| a In chloroform b Fluorescence quantum yields in CHCl3 in comparison to 3,4,9,10-perylenetetracarbonic acid tetramethylester | 
11.3.3
 13 октября, 2015
 13 октября, 2015  Pokraskin
 Pokraskin  Опубликовано в рубрике
 Опубликовано в рубрике 