2012
DOI: 10.1021/om3000407
|View full text |Cite
|
Sign up to set email alerts
|

Structure–Property Studies of Bichromophoric, PAH-Functionalized Dithieno[3,2-b:2′,3′-d]phospholes

Abstract: A series of dithienophospholes featuring polyaromatic hydrocarbon (PAH) substituents, with increasing number of fused rings ranging from 2 to 4 at the phosphorus center, have been synthesized and characterized. The installation of a large π-system in the vicinity of the dithienophosphole scaffold was found to induce unusual photophysics for this system that are based on the creation of two neighboring chromophores within the same molecular scaffold. Extensive photophysical studies revealed that significant ene… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
2
1

Citation Types

1
14
0

Year Published

2012
2012
2015
2015

Publication Types

Select...
7

Relationship

3
4

Authors

Journals

citations
Cited by 21 publications
(15 citation statements)
references
References 77 publications
1
14
0
Order By: Relevance
“…Upon excitation into the transition band at about 308–382 nm of compounds 1 – 6 in degassed benzene solution at room temperature, the compounds display intense blue to greenish‐yellow luminescence at about 456–472 nm and the lifetimes of the compounds are found to be in the nanosecond range. The Stokes shifts of the compounds varied from 4765 to 5762 cm −1 9b. 20 Parallel to the electronic absorption study, the emission bands of the electron‐donating group‐substituted phosphole ( 4 ) and the electron‐withdrawing group‐substituted phospholes (compounds 1 and 2 ) occur at lower energy than that of the unsubstituted counterpart, as shown in Figure 6…”
Section: Resultsmentioning
confidence: 88%
“…Upon excitation into the transition band at about 308–382 nm of compounds 1 – 6 in degassed benzene solution at room temperature, the compounds display intense blue to greenish‐yellow luminescence at about 456–472 nm and the lifetimes of the compounds are found to be in the nanosecond range. The Stokes shifts of the compounds varied from 4765 to 5762 cm −1 9b. 20 Parallel to the electronic absorption study, the emission bands of the electron‐donating group‐substituted phosphole ( 4 ) and the electron‐withdrawing group‐substituted phospholes (compounds 1 and 2 ) occur at lower energy than that of the unsubstituted counterpart, as shown in Figure 6…”
Section: Resultsmentioning
confidence: 88%
“…This 86 nm redshift suggests the presence of an intermolecular π–π interaction very likely due to the exposed linear terthienyl moiety that results in excimer emission at higher concentrations 19. It is important to mention that this type of behavior was not as pronounced, if observed at all, in related P ‐pyrenyl dithienophospholes,13a even though pyrene itself readily forms excimers20 at high concentrations. The blueshifted solid‐state emission of 4 relative to that as a solution in highly concentrated CH 2 Cl 2 can be attributed to the fact that formation of excimers in solution requires an appropriate intermolecular alignment of two species (possibly with different conformations) to aggregate,19 which may not be available in the solid state.…”
Section: Resultsmentioning
confidence: 91%
“…29 In contrast, indolocarbazole-substituted 3e showed a slightly downeld-shied 31 P NMR resonance at d ¼ 22.2 ppm that is, however, in line with related systems exhibiting exocyclic polyaromatic hydrocarbon (PAH) substituents. 30 By contrast, ortho-derivative 3c featured a signicantly upeld-shied 31 P NMR chemical shi at d ¼ 12.9 ppm compared to its congeners 3a and 3b, indicating a distinctively different chemical environment of the phosphorus atom for this particular conguration. In all cases, the n-butyl substituents at the dithienophosphole core led to slightly (1-3 ppm) downeld-shied resonances, which is in accordance with previous ndings.…”
Section: Synthesis and Characterizationmentioning
confidence: 95%
“…Nevertheless, interactions between the s*-orbital of the exocyclic bond and the p*-system of the ring lead to a certain degree of aromaticity and a high polarizability of the phosphole system. 23,24 The resulting high tunability of the photo-physical and electro-chemical properties by chemical modication 22,23,25 suggested the utility of this versatile building block for the elds of luminescent materials, [26][27][28][29][30][31] polymers, [32][33][34] coordination chemistry 26,35 and selforganizing materials. 36,37 In particular, oxidation of the phosphorus center is an appealing strategy to signicantly enhance the electron-accepting properties of the dithieno[3,2-b:2 0 ,3 0 -d] phosphole moiety, 21,24 which enables the application of this scaffold in donor-acceptor type materials.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation