Abstract
A series of organic- and water-soluble distyrylbenzene-based two-photon absorption (TPA) fluorophores containing dialkylamino donor groups at the termini was designed, synthesized, and characterized. The central core was systematically substituted to modulate intramolecular charge transfer (ICT). These molecules allow an examination of solvent effects on the TPA cross section (δ) and on the TPA action cross section. In toluene, the δ values follow the order of ICT strength. The effect of solvent on δ is nonmonotonic: maximum δ was measured in an intermediate polarity solvent (THF) and was lowest in water. We failed to find a correlation between the observed solvent effect and previous theoretical predictions. Hydrogen bonding to the donor groups and aggregation of the optical units in water, which are not included in calculational analysis, may be responsible for the discrepancies between experimental results and theory.
| Original language | English |
|---|---|
| Pages (from-to) | 14721-14729 |
| Number of pages | 9 |
| Journal | Journal of the American Chemical Society |
| Volume | 127 |
| Issue number | 42 |
| DOIs | |
| Publication status | Published - 2005 Nov 1 |
| Externally published | Yes |
Fingerprint
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Solvent effects on the two-photon absorption of distyrylbenzene chromophores. / Woo, Han Young; Liu, Bin; Kohler, Bernhard; Korystov, Dmitry; Mikhailovsky, Alexander; Bazan, Guillermo C.
In: Journal of the American Chemical Society, Vol. 127, No. 42, 01.11.2005, p. 14721-14729.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Solvent effects on the two-photon absorption of distyrylbenzene chromophores
AU - Woo, Han Young
AU - Liu, Bin
AU - Kohler, Bernhard
AU - Korystov, Dmitry
AU - Mikhailovsky, Alexander
AU - Bazan, Guillermo C.
PY - 2005/11/1
Y1 - 2005/11/1
N2 - A series of organic- and water-soluble distyrylbenzene-based two-photon absorption (TPA) fluorophores containing dialkylamino donor groups at the termini was designed, synthesized, and characterized. The central core was systematically substituted to modulate intramolecular charge transfer (ICT). These molecules allow an examination of solvent effects on the TPA cross section (δ) and on the TPA action cross section. In toluene, the δ values follow the order of ICT strength. The effect of solvent on δ is nonmonotonic: maximum δ was measured in an intermediate polarity solvent (THF) and was lowest in water. We failed to find a correlation between the observed solvent effect and previous theoretical predictions. Hydrogen bonding to the donor groups and aggregation of the optical units in water, which are not included in calculational analysis, may be responsible for the discrepancies between experimental results and theory.
AB - A series of organic- and water-soluble distyrylbenzene-based two-photon absorption (TPA) fluorophores containing dialkylamino donor groups at the termini was designed, synthesized, and characterized. The central core was systematically substituted to modulate intramolecular charge transfer (ICT). These molecules allow an examination of solvent effects on the TPA cross section (δ) and on the TPA action cross section. In toluene, the δ values follow the order of ICT strength. The effect of solvent on δ is nonmonotonic: maximum δ was measured in an intermediate polarity solvent (THF) and was lowest in water. We failed to find a correlation between the observed solvent effect and previous theoretical predictions. Hydrogen bonding to the donor groups and aggregation of the optical units in water, which are not included in calculational analysis, may be responsible for the discrepancies between experimental results and theory.
UR - http://www.scopus.com/inward/record.url?scp=27144548434&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=27144548434&partnerID=8YFLogxK
U2 - 10.1021/ja052906g
DO - 10.1021/ja052906g
M3 - Article
C2 - 16231926
AN - SCOPUS:27144548434
VL - 127
SP - 14721
EP - 14729
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 42
ER -