Tetraphenylethylenepyrrolo[3,2- b]pyrrole Hybrids as Solid-State Emitters: The Role of Substitution Pattern

Bartłomiej Sadowski; Khaled Hassanein; Barbara Ventura; Daniel T. Gryko

doi:10.1021/acs.orglett.8b01011

Tetraphenylethylenepyrrolo[3,2- b]pyrrole Hybrids as Solid-State Emitters: The Role of Substitution Pattern

Bartłomiej Sadowski, Khaled Hassanein, Barbara Ventura^*, Daniel T. Gryko

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

Abstract

Two hybrid dyes possessing tetraphenylethylene moieties weakly conjugated with a pyrrolo[3,2-b]pyrrole core have been synthesized. Both dyes display a weak emission in solution, however, in the solid state a ∼100-fold increase in the fluorescence quantum yield is observed. The position of the molecular rotors about the core greatly influences the photophysical characteristics. The variances in emission properties were assigned to entirely different changes in dihedral angles upon excitation, which in turn have substantial effects on radiative rate constants, allowed transitions, and HOMO/LUMO distribution.

Original language	English
Pages (from-to)	3183-3186
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.8b01011
State	Published - 1 Jun 2018
Externally published	Yes

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Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Tetraphenylethylenepyrrolo[3,2- b]pyrrole Hybrids as Solid-State Emitters: The Role of Substitution Pattern",

abstract = "Two hybrid dyes possessing tetraphenylethylene moieties weakly conjugated with a pyrrolo[3,2-b]pyrrole core have been synthesized. Both dyes display a weak emission in solution, however, in the solid state a ∼100-fold increase in the fluorescence quantum yield is observed. The position of the molecular rotors about the core greatly influences the photophysical characteristics. The variances in emission properties were assigned to entirely different changes in dihedral angles upon excitation, which in turn have substantial effects on radiative rate constants, allowed transitions, and HOMO/LUMO distribution.",

author = "Bart{\l}omiej Sadowski and Khaled Hassanein and Barbara Ventura and Gryko, \{Daniel T.\}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b01011",

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T2 - The Role of Substitution Pattern

AU - Sadowski, Bartłomiej

AU - Hassanein, Khaled

AU - Ventura, Barbara

AU - Gryko, Daniel T.

PY - 2018/6/1

Y1 - 2018/6/1

N2 - Two hybrid dyes possessing tetraphenylethylene moieties weakly conjugated with a pyrrolo[3,2-b]pyrrole core have been synthesized. Both dyes display a weak emission in solution, however, in the solid state a ∼100-fold increase in the fluorescence quantum yield is observed. The position of the molecular rotors about the core greatly influences the photophysical characteristics. The variances in emission properties were assigned to entirely different changes in dihedral angles upon excitation, which in turn have substantial effects on radiative rate constants, allowed transitions, and HOMO/LUMO distribution.

AB - Two hybrid dyes possessing tetraphenylethylene moieties weakly conjugated with a pyrrolo[3,2-b]pyrrole core have been synthesized. Both dyes display a weak emission in solution, however, in the solid state a ∼100-fold increase in the fluorescence quantum yield is observed. The position of the molecular rotors about the core greatly influences the photophysical characteristics. The variances in emission properties were assigned to entirely different changes in dihedral angles upon excitation, which in turn have substantial effects on radiative rate constants, allowed transitions, and HOMO/LUMO distribution.

UR - https://www.scopus.com/pages/publications/85048056055

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DO - 10.1021/acs.orglett.8b01011

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JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Tetraphenylethylenepyrrolo[3,2- b]pyrrole Hybrids as Solid-State Emitters: The Role of Substitution Pattern

Abstract

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