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Chasing BODIPY: Enhancement of luminescence in homoleptic bis(dipyrrinato) Zn II complexes utilizing symmetric and unsymmetrical dipyrrins

Chasing BODIPY: Enhancement of luminescence in homoleptic bis(dipyrrinato) Zn II complexes utilizing symmetric and unsymmetrical dipyrrins
Chasing BODIPY: Enhancement of luminescence in homoleptic bis(dipyrrinato) Zn II complexes utilizing symmetric and unsymmetrical dipyrrins

Dipyrromethene metal complexes are fascinating molecules that have applications as light-harvesting systems, luminophores, and laser dyes. Recently, it has been shown that structurally rigid bis(dipyrrinato) zinc(II) complexes exhibit high fluorescence with comparable quantum yields to those of boron dipyrromethenes or BODIPYs. Herein, eight new bis(dipyrrinato) Zn II complexes, obtained from symmetric and unsymmetrical functionalization of the dipyrromethene structure through a Knoevenagel reaction, are reported. It was possible not only to vary the maximum visible absorption from 490 to 630 nm, but also to enhance the emission quantum yield up to 66 %, which is extraordinarily high for homoleptic bis(dipyrrinato) zinc complexes. These results pave the way for designing highly luminescent bis(dipyrrinato) zinc complexes.

dipyrromethene ligands, Knoevenagel condensation, light-harvesting chromophores, luminescence, zinc
0947-6539
3816-3827
Tungulin, Dmitry
1dfd63b9-deac-4e29-97d9-a1674593bb68
Leier, Julia
9458fc35-6f8f-4927-b591-1cb06a4a1f82
Carter, Anthony B.
716d0f93-55b4-497e-9081-8e84b7104b65
Powell, Annie K.
84c3aa9f-b469-489c-a4d7-264c4ec39e44
Albuquerque, Rodrigo Q.
eda2d38b-6800-419f-a04a-f8281283cf94
Unterreiner, Andreas N.
9f6b81a0-3e03-4597-bfbd-221c0454e758
Bizzarri, Claudia
421f65d2-5eed-4f2a-9544-10baee0574ea
Tungulin, Dmitry
1dfd63b9-deac-4e29-97d9-a1674593bb68
Leier, Julia
9458fc35-6f8f-4927-b591-1cb06a4a1f82
Carter, Anthony B.
716d0f93-55b4-497e-9081-8e84b7104b65
Powell, Annie K.
84c3aa9f-b469-489c-a4d7-264c4ec39e44
Albuquerque, Rodrigo Q.
eda2d38b-6800-419f-a04a-f8281283cf94
Unterreiner, Andreas N.
9f6b81a0-3e03-4597-bfbd-221c0454e758
Bizzarri, Claudia
421f65d2-5eed-4f2a-9544-10baee0574ea

Tungulin, Dmitry, Leier, Julia, Carter, Anthony B., Powell, Annie K., Albuquerque, Rodrigo Q., Unterreiner, Andreas N. and Bizzarri, Claudia (2019) Chasing BODIPY: Enhancement of luminescence in homoleptic bis(dipyrrinato) Zn II complexes utilizing symmetric and unsymmetrical dipyrrins. Chemistry - A European Journal, 25 (15), 3816-3827. (doi:10.1002/chem.201806330).

Record type: Article

Abstract

Dipyrromethene metal complexes are fascinating molecules that have applications as light-harvesting systems, luminophores, and laser dyes. Recently, it has been shown that structurally rigid bis(dipyrrinato) zinc(II) complexes exhibit high fluorescence with comparable quantum yields to those of boron dipyrromethenes or BODIPYs. Herein, eight new bis(dipyrrinato) Zn II complexes, obtained from symmetric and unsymmetrical functionalization of the dipyrromethene structure through a Knoevenagel reaction, are reported. It was possible not only to vary the maximum visible absorption from 490 to 630 nm, but also to enhance the emission quantum yield up to 66 %, which is extraordinarily high for homoleptic bis(dipyrrinato) zinc complexes. These results pave the way for designing highly luminescent bis(dipyrrinato) zinc complexes.

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More information

e-pub ahead of print date: 28 January 2019
Published date: 12 March 2019
Keywords: dipyrromethene ligands, Knoevenagel condensation, light-harvesting chromophores, luminescence, zinc

Identifiers

Local EPrints ID: 430383
URI: http://eprints.soton.ac.uk/id/eprint/430383
ISSN: 0947-6539
PURE UUID: 7272a558-3444-4605-b914-c9b26ad473fc

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Date deposited: 26 Apr 2019 16:30
Last modified: 14 Sep 2021 20:20

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Contributors

Author: Dmitry Tungulin
Author: Julia Leier
Author: Anthony B. Carter
Author: Annie K. Powell
Author: Rodrigo Q. Albuquerque
Author: Andreas N. Unterreiner
Author: Claudia Bizzarri

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