TY  - JOUR
A1  - Weclawski, Marek K.
A1  - Meiling, Till Thomas
A1  - Leniak, Arkadiusz
A1  - Cywinski, Piotr J.
A1  - Gryko, Daniel T.
T1  - Planar, Fluorescent Push-Pull System That Comprises Benzofuran and Iminocoumarin Moieties
JF  - Organic letters
N2  - Previously unknown, vertically linked heterocycles comprised of benzofuran and iminocoumarin moieties have been synthesized directly from 1,5-dibenzoyloxyanthraquinone and arylacetonitriles via double Knoevenagel condensation followed by formal HCN elimination. The structural assembly of fully conjugated, electron-rich benzofuran and electron-deficient iminocoumarin is responsible for the strongly polarized nature of these heterocycles which translates into their polarity-sensitive fluorescence.
Y1  - 2015
U6  - https://doi.org/10.1021/acs.orglett.5b02042
SN  - 1523-7060
SN  - 1523-7052
VL  - 17
IS  - 17
SP  - 4252
EP  - 4255
PB  - American Chemical Society
CY  - Washington
ER  - 
TY  - JOUR
A1  - Nazir, Rashid
A1  - Meiling, Till Thomas
A1  - Cywinski, Piotr J.
A1  - Gryko, Daniel T.
T1  - Synthesis and Optical Properties of alpha,beta-Unsaturated Ketones Bearing a Benzofuran Moiety
JF  - Asian journal of organic chemistry : an ACES journal
N2  - Five pi-expanded alpha,beta-unsaturated ketones have been prepared from a strongly electron-rich benzofuran derivative via Knoevenagel reaction and aldol condensation. The incorporation of two 6-didodecylaminobenzofuran-2-yl groups at the periphery of D-pi-A and D-pi-A-pi-D molecules resulted in dyes with excellent solubility in the majority of organic solvents. In contrast to the majority of alpha,beta-unsaturated ketones, these dyes emit relatively strongly in the red region with a fluorescence quantum yield up to 40%. They also display strong solvatofluorochromism with emission shifting from 570 nm in toluene to 670 nm in CHCl3. Depending on the chemical structure, they two-photon cross-sections (sigma(2)) are up to 1700 GM (1 GM=10(50) cm(4)s photon(-1)).
KW  - aldol reaction
KW  - benzofurans
KW  - fluorescence
KW  - ketones
KW  - two-photon absorption
Y1  - 2015
U6  - https://doi.org/10.1002/ajoc.201500242
SN  - 2193-5807
SN  - 2193-5815
VL  - 4
IS  - 9
SP  - 929
EP  - 935
PB  - Wiley-VCH
CY  - Weinheim
ER  -