Design, synthesis, photophysical properties and pH-sensing application of pyrimidine-phthalimide derivativesElectronic supplementary information (ESI) available: Experimental details and characterization data and CIF. CCDC 1566171 and 1566173. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7tc03472e
On the basis of the molecular design of the donor-π-acceptor (D-π-A) pyrimidine-phthalimide derivatives, two new atypical AIE chromophores, 2-(4,6-dimethylpyrimidin-2-yl)isoindoline-1,3-dione ( PB ) and 2-(4,6-bis(4-(dimethylamino)styryl)pyrimidin-2-yl)isoindoline-1,3-dione ( NPB ), were synthesized...
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Published |
19.10.2017
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Abstract | On the basis of the molecular design of the donor-π-acceptor (D-π-A) pyrimidine-phthalimide derivatives, two new atypical AIE chromophores, 2-(4,6-dimethylpyrimidin-2-yl)isoindoline-1,3-dione (
PB
) and 2-(4,6-bis(4-(dimethylamino)styryl)pyrimidin-2-yl)isoindoline-1,3-dione (
NPB
), were synthesized and characterized by using IR,
1
H NMR,
13
C NMR and HRMS. Both
PB
and
NPB
exhibited obvious solid-state fluorescence emission due to their twisted geometries and positive solvatochromism due to their different molecular conformations in various solvents. Owing to the different push-pull electronic effects of substituents on the pyrimidine moiety,
PB
and
NPB
, acting as D-π-A compounds, showed different HOMO-LUMO gaps and a variable red-shifted emission in their solid state, substantiating the possibility to tune effectively the photophysical properties of these AIE chromophores by rational molecular design. In addition,
PB
and
NPB
could be easily and reversibly protonated at the site of the nitrogen atoms, causing dramatic color changes. This phenomenon opens up the potential avenues of developing novel colorimetric pH sensors and logic gates for specific applications.
Using molecular design of donor-π-acceptor pyrimidine-phthalimide derivatives, two new atypical AIE chromophores were synthesized and characterized using IR,
1
H NMR,
13
C NMR and HRMS. |
---|---|
AbstractList | On the basis of the molecular design of the donor-π-acceptor (D-π-A) pyrimidine-phthalimide derivatives, two new atypical AIE chromophores, 2-(4,6-dimethylpyrimidin-2-yl)isoindoline-1,3-dione (
PB
) and 2-(4,6-bis(4-(dimethylamino)styryl)pyrimidin-2-yl)isoindoline-1,3-dione (
NPB
), were synthesized and characterized by using IR,
1
H NMR,
13
C NMR and HRMS. Both
PB
and
NPB
exhibited obvious solid-state fluorescence emission due to their twisted geometries and positive solvatochromism due to their different molecular conformations in various solvents. Owing to the different push-pull electronic effects of substituents on the pyrimidine moiety,
PB
and
NPB
, acting as D-π-A compounds, showed different HOMO-LUMO gaps and a variable red-shifted emission in their solid state, substantiating the possibility to tune effectively the photophysical properties of these AIE chromophores by rational molecular design. In addition,
PB
and
NPB
could be easily and reversibly protonated at the site of the nitrogen atoms, causing dramatic color changes. This phenomenon opens up the potential avenues of developing novel colorimetric pH sensors and logic gates for specific applications.
Using molecular design of donor-π-acceptor pyrimidine-phthalimide derivatives, two new atypical AIE chromophores were synthesized and characterized using IR,
1
H NMR,
13
C NMR and HRMS. |
Author | Li, Baoyan Meng, Xinlei Ge, Shusheng Lu, Yun Yan, Han |
AuthorAffiliation | Department of Polymer Science and Engineering Ministry of Education State Key Laboratory of Coordination Chemistry Collaborative Innovation Center of Chemistry for Life Sciences Key Laboratory of High Performance Polymer Materials and Technology (Nanjing University) Nanjing University School of Chemistry and Chemical Engineering |
AuthorAffiliation_xml | – name: School of Chemistry and Chemical Engineering – name: Nanjing University – name: Collaborative Innovation Center of Chemistry for Life Sciences – name: Department of Polymer Science and Engineering – name: State Key Laboratory of Coordination Chemistry – name: Ministry of Education – name: Key Laboratory of High Performance Polymer Materials and Technology (Nanjing University) |
Author_xml | – sequence: 1 givenname: Han surname: Yan fullname: Yan, Han – sequence: 2 givenname: Xinlei surname: Meng fullname: Meng, Xinlei – sequence: 3 givenname: Baoyan surname: Li fullname: Li, Baoyan – sequence: 4 givenname: Shusheng surname: Ge fullname: Ge, Shusheng – sequence: 5 givenname: Yun surname: Lu fullname: Lu, Yun |
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Notes | For ESI and crystallographic data in CIF or other electronic format see DOI 1566171 Electronic supplementary information (ESI) available: Experimental details and characterization data and CIF. CCDC and 10.1039/c7tc03472e 1566173 |
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Title | Design, synthesis, photophysical properties and pH-sensing application of pyrimidine-phthalimide derivativesElectronic supplementary information (ESI) available: Experimental details and characterization data and CIF. CCDC 1566171 and 1566173. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7tc03472e |
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