2011
DOI: 10.1063/1.3563801
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Bond alternation, polarizability, and resonance detuning in methine dyes

Abstract: We derive structure-property relationships for methine ("Brooker") dyes relating the color of the dye and its symmetric parents to its bond alternation in the ground state and also to the dipole properties associated with its low-lying charge-resonance (or charge-transfer) transition. We calibrate and test these relationships on an array of different protonation states of the green fluorescent protein chromophore motif (an asymmetric halochromic methine dye) and its symmetric parent dyes. The relationships rel… Show more

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Cited by 27 publications
(52 citation statements)
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“…33,45,48 A similar, even broader, analogy can also be found within the active space of the analogous two-state SA2-CAS(4,3) solutions. 44,60,72 Both these dyes and GFP chromophores display a common binding-dependent fluorescence enhancement associated with the suppression of a common double-bond photoisomerization chemistry in the excited state. [4][5][6][7][73][74][75] Our ongoing work shows that this analogy can also be applied to electronic structure along the photoisomerization coordinates of some of the dyes studied here.…”
Section: A General Discussionmentioning
confidence: 99%
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“…33,45,48 A similar, even broader, analogy can also be found within the active space of the analogous two-state SA2-CAS(4,3) solutions. 44,60,72 Both these dyes and GFP chromophores display a common binding-dependent fluorescence enhancement associated with the suppression of a common double-bond photoisomerization chemistry in the excited state. [4][5][6][7][73][74][75] Our ongoing work shows that this analogy can also be applied to electronic structure along the photoisomerization coordinates of some of the dyes studied here.…”
Section: A General Discussionmentioning
confidence: 99%
“…The protocol we use here is essentially the same as that we have used in our studies of the chemically related green fluorescent protein (GFP) chromophore system. 44, 45 The importance and utility of three-orbital models of the electronic structure of GFP chromophores have been highlighted in the work of independent research groups via distinct electronic structure approaches. 46 Their work provides a strong support for the contention that the four-electron three-orbital problem is a good model of the electronic structure of diarylmethanes.…”
Section: A Computationsmentioning
confidence: 99%
“…77 The SA2-CAS(4,3) electronic structure model that we use here has been previously applied to the electronic structure of GFP chromophore models. 48,49 The active spaces are shown in Figure 1, using the Boys(-Edminston-Ruedenberg) orbital representation. 78,79 The active space structure is analogous to an allylic π -electron system.…”
Section: B Computational Quantum Chemistrymentioning
confidence: 99%
“…48, 49 The effects of protonation on the twisting pathways are qualitative; protonation at the phenolic oxygen is sufficient to effectively remove one of two possible twisting channels, and also eliminates the twist-dependence of the excited-state charge localization. 38,50 Experimentally, the viscosity dependence of the decay of synthetic GFP chromophore models is weak.…”
Section: Introductionmentioning
confidence: 99%
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