Acid/base-triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic helicenes

Nidal Saleh; Barry Moore; Monika Srebro; Nicolas Vanthuyne; Loïc Toupet; J. A.Gareth Williams; Christian Roussel; Kirandeep K. Deol; Gilles Muller; Jochen Autschbach; Jeanne Crassous

doi:10.1002/chem.201405176

Acid/base-triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic helicenes

Nidal Saleh
, Barry Moore
, Monika Srebro
, Nicolas Vanthuyne
, Loïc Toupet
, J. A.Gareth Williams
, Christian Roussel
, Kirandeep K. Deol
, Gilles Muller
, Jochen Autschbach
, Jeanne Crassous

Chemistry

Institut des Sciences Chimiques de Rennes
SUNY Buffalo
Jagiellonian University in Kraków
Aix Marseille University
Durham University
San Jose State University

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

180 Scopus citations

Abstract

Electronic circular dichroism and circularly polarized luminescence acid/base switching activity has been demonstrated in helicene-bipyridine proligand 1a and in its "rollover" cycloplatinated derivative 2a. Whereas proligand1a displays a strong bathochromic shift (> 160 nm) of the nonpolarized and circularly polarized luminescence upon protonation, complex 2a displays slightly stronger emission. This strikingly different behavior between singlet emission in the organic helicene and triplet emission in the organometallic derivative has been rationalized by using quantumchemical calculations. The very large bathochromic shift of the emission observed upon protonation of azahelicene-bipyridine1a has been attributed to the decrease in aromaticity (promoting a charge-transfer-type transition rather than a transition) as well as an increase in the HOMO-LUMO character of the transition and stabilization of the LUMO level upon protonation.

Original language	English
Pages (from-to)	1673-1681
Number of pages	9
Journal	Chemistry - A European Journal
Volume	21
Issue number	4
DOIs	https://doi.org/10.1002/chem.201405176
State	Published - Jan 19 2015

Keywords

Circular dichroism
Density functional calculations
Helicenes
Luminescence
Switches

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10.1002/chem.201405176

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Saleh, N., Moore, B., Srebro, M., Vanthuyne, N., Toupet, L., Williams, J. A. G., Roussel, C., Deol, K. K., Muller, G., Autschbach, J., & Crassous, J. (2015). Acid/base-triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic helicenes. Chemistry - A European Journal, 21(4), 1673-1681. https://doi.org/10.1002/chem.201405176

@article{3960ffc7a6cd4f48a03879ddbca538df,

title = "Acid/base-triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic helicenes",

abstract = "Electronic circular dichroism and circularly polarized luminescence acid/base switching activity has been demonstrated in helicene-bipyridine proligand 1a and in its {"}rollover{"} cycloplatinated derivative 2a. Whereas proligand1a displays a strong bathochromic shift (> 160 nm) of the nonpolarized and circularly polarized luminescence upon protonation, complex 2a displays slightly stronger emission. This strikingly different behavior between singlet emission in the organic helicene and triplet emission in the organometallic derivative has been rationalized by using quantumchemical calculations. The very large bathochromic shift of the emission observed upon protonation of azahelicene-bipyridine1a has been attributed to the decrease in aromaticity (promoting a charge-transfer-type transition rather than a transition) as well as an increase in the HOMO-LUMO character of the transition and stabilization of the LUMO level upon protonation.",

keywords = "Circular dichroism, Density functional calculations, Helicenes, Luminescence, Switches",

author = "Nidal Saleh and Barry Moore and Monika Srebro and Nicolas Vanthuyne and Lo{\"i}c Toupet and Williams, \{J. A.Gareth\} and Christian Roussel and Deol, \{Kirandeep K.\} and Gilles Muller and Jochen Autschbach and Jeanne Crassous",

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year = "2015",

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doi = "10.1002/chem.201405176",

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Saleh, N, Moore, B, Srebro, M, Vanthuyne, N, Toupet, L, Williams, JAG, Roussel, C, Deol, KK, Muller, G, Autschbach, J & Crassous, J 2015, 'Acid/base-triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic helicenes', Chemistry - A European Journal, vol. 21, no. 4, pp. 1673-1681. https://doi.org/10.1002/chem.201405176

TY - JOUR

T1 - Acid/base-triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic helicenes

AU - Saleh, Nidal

AU - Moore, Barry

AU - Srebro, Monika

AU - Vanthuyne, Nicolas

AU - Toupet, Loïc

AU - Williams, J. A.Gareth

AU - Roussel, Christian

AU - Deol, Kirandeep K.

AU - Muller, Gilles

AU - Autschbach, Jochen

AU - Crassous, Jeanne

PY - 2015/1/19

Y1 - 2015/1/19

N2 - Electronic circular dichroism and circularly polarized luminescence acid/base switching activity has been demonstrated in helicene-bipyridine proligand 1a and in its "rollover" cycloplatinated derivative 2a. Whereas proligand1a displays a strong bathochromic shift (> 160 nm) of the nonpolarized and circularly polarized luminescence upon protonation, complex 2a displays slightly stronger emission. This strikingly different behavior between singlet emission in the organic helicene and triplet emission in the organometallic derivative has been rationalized by using quantumchemical calculations. The very large bathochromic shift of the emission observed upon protonation of azahelicene-bipyridine1a has been attributed to the decrease in aromaticity (promoting a charge-transfer-type transition rather than a transition) as well as an increase in the HOMO-LUMO character of the transition and stabilization of the LUMO level upon protonation.

AB - Electronic circular dichroism and circularly polarized luminescence acid/base switching activity has been demonstrated in helicene-bipyridine proligand 1a and in its "rollover" cycloplatinated derivative 2a. Whereas proligand1a displays a strong bathochromic shift (> 160 nm) of the nonpolarized and circularly polarized luminescence upon protonation, complex 2a displays slightly stronger emission. This strikingly different behavior between singlet emission in the organic helicene and triplet emission in the organometallic derivative has been rationalized by using quantumchemical calculations. The very large bathochromic shift of the emission observed upon protonation of azahelicene-bipyridine1a has been attributed to the decrease in aromaticity (promoting a charge-transfer-type transition rather than a transition) as well as an increase in the HOMO-LUMO character of the transition and stabilization of the LUMO level upon protonation.

KW - Circular dichroism

KW - Density functional calculations

KW - Helicenes

KW - Luminescence

KW - Switches

UR - https://www.scopus.com/pages/publications/84920964673

U2 - 10.1002/chem.201405176

DO - 10.1002/chem.201405176

M3 - Article

C2 - 25529335

AN - SCOPUS:84920964673

SN - 0947-6539

VL - 21

SP - 1673

EP - 1681

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 4

ER -

Acid/base-triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic helicenes

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