Protein-induced fluorescence enhancement of two-photon excitable water-soluble diketopyrrolopyrroles

Tang, S. Y.; Zadeh, Ebrahim H. Ghazvini; Kim, Bosung; Toomey, Nikia T; Bondar, Mykhailo V.; Belfield, Kevin D.

doi:10.1039/c7ob01397c

“…In order to have the DPP compounds solvated in water, their polarity needs to be enhanced by the addition of ionic functional groups 51 or in some cases also by carboxylic acid functional groups. 52 The absence of any such functional groups in the simulated polymers leads to the low solubility in water. In contrast, the addition of alkyl side chains, as has been implemented in the present simulations, enhances the solubility in organic solvents.…”

Section: Resultsmentioning

confidence: 99%

“…It has been well established that the intramolecular hydrogen bonding in the DPP compounds hinders its solubility in any kind of solvent. In order to have the DPP compounds solvated in water, their polarity needs to be enhanced by the addition of ionic functional groups or in some cases also by carboxylic acid functional groups . The absence of any such functional groups in the simulated polymers leads to the low solubility in water.…”

Section: Resultsmentioning

confidence: 99%

Development and Testing of an All-Atom Force Field for Diketopyrrolopyrrole Polymers with Conjugated Substituents

Sundaram

¹

,

Lyulin

²

,

Baumeier

³

2020

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We develop an all-atom force field for a series of diketopyrrolopyrrole polymers with two aromatic pyridine substituents and a variable number of π-conjugated thiophene units in the backbone (DPP2Py m T), used as donor materials in organic photovoltaic devices. Available intrafragment parameterizations of the individual fragment building blocks are combined with interfragment bonded and nonbonded parameters explicitly derived from density functional theory calculations. To validate the force field, we perform classical molecular dynamics simulations of single polymer chains with m = 1, 2, 3 in good and bad solvents and of melts. We observe the expected dependence of the chain conformation on the solvent quality, with the chain collapsing in water, and swelling in chloroform. The glass-transition temperature for the polymer melts is found to be in the range of 340–370 K. Analysis of the mobility of the conjugated segments in the polymer backbone reveals two relaxation processes: a fast one with a characteristic time at room temperature on the order of 10 ps associated with nearly harmonic vibrations and a slow one on the order of 100 ns associated with temperature-activated cis–trans transitions.

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“…In order to have the DPP compounds solvated in water their polarity needs to be enhanced by the addition of ionic functional groups, 47 or in some cases also by carboxylic acid functional groups. 48 The absence of any such functional groups in the simulated polymers leads to the low solubility in water. In contrast, the addition of alkyl side chains, as has been implemented in the present simulations enhances the solubility in organic solvents.…”

Section: B Np-dpp2pymt In Solutionmentioning

confidence: 99%

Development and Testing of an All-Atom Force Field for Diketopyrrolopyrrole Polymers with Conjugated Substituents

Sundaram¹,

Lyulin²,

Baumeier³

2020

Preprint

0

View full text Add to dashboard Cite

We develop an all-atom force field for a series of diketopyrrolopyrrole polymers with two aromatic pyridine substituents and variable number of pi-conjugated thiophene units in the backbone, used as donor material in organic photovoltaic devices. Available intra-fragment parameterizations of the individual fragment building blocks are combined with inter-fragment bonded and non-bonded parameters explicitly derived from density-functional theory calculations. To validate the force field we perform classical molecular dynamics simulations of single polymer chains with 1, 2, and 3 thiophenes in good and bad solvents, and of melts. We observe the expected dependence of the chain conformation on the solvent quality, with the chain collapsing in water, and swelling in chloroform. The glass transition temperature for the polymer melts is found to be in the range of 340K to 370K. Analysis of the mobility of the conjugated segments in the polymer backbone reveals two relaxation processes: a fast one with a characteristic time at room temperature on the order of 10ps associated with nearly harmonic vibrations and a slow one on the order of 100 associated with temperature activated cis-trans transitions.

show abstract

“…ionic functional groups, 51 or in some cases also by carboxylic acid functional groups. 52 The absence of any such functional groups in the simulated polymers leads to the low solubility in water. In contrast, the addition of alkyl side chains, as has been implemented in the present simulations enhances the solubility in organic solvents.…”

Section: N P -Dpp2pymt In Solutionmentioning

confidence: 99%

Development and Testing of an All-Atom Force Field for Diketopyrrolopyrrole Polymers with Conjugated Substituents

Sundaram¹,

Lyulin²,

Baumeier³

2020

Preprint

0

View full text Add to dashboard Cite

We develop an all-atom force field for a series of diketopyrrolopyrrole polymers with two aromatic pyridine substituents and variable number of pi-conjugated thiophene units in the backbone, used as donor material in organic photovoltaic devices. Available intra-fragment parameterizations of the individual fragment building blocks are combined with inter-fragment bonded and non-bonded parameters explicitly derived from density-functional theory calculations. To validate the force field we perform classical molecular dynamics simulations of single polymer chains with 1, 2, and 3 thiophenes in good and bad solvents, and of melts. We observe the expected dependence of the chain conformation on the solvent quality, with the chain collapsing in water, and swelling in chloroform. The glass transition temperature for the polymer melts is found to be in the range of 340K to 370K. Analysis of the mobility of the conjugated segments in the polymer backbone reveals two relaxation processes: a fast one with a characteristic time at room temperature on the order of 10ps associated with nearly harmonic vibrations and a slow one on the order of 100 associated with temperature activated cis-trans transitions.

show abstract

Protein-induced fluorescence enhancement of two-photon excitable water-soluble diketopyrrolopyrroles

Cited by 14 publications

References 46 publications

Development and Testing of an All-Atom Force Field for Diketopyrrolopyrrole Polymers with Conjugated Substituents

Development and Testing of an All-Atom Force Field for Diketopyrrolopyrrole Polymers with Conjugated Substituents

Development and Testing of an All-Atom Force Field for Diketopyrrolopyrrole Polymers with Conjugated Substituents

Development and Testing of an All-Atom Force Field for Diketopyrrolopyrrole Polymers with Conjugated Substituents

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