Dataset Information

Donor-Acceptor Dyads and Triads Employing Core-Substituted Naphthalene Diimides: A Synthetic and Spectro (Electrochemical) Study.

ABSTRACT: Donor-acceptor dyads and triads comprising core-substituted naphthalene diimide (NDI) chromophores and either phenothiazine or phenoxazine donors are described. Synthesis combined with electrochemical and spectroelectrochemical investigations facilitates characterisation of the various redox states of these molecules, confirming the ability to combine arrays of electron donating and accepting moieties into single species that retain the redox properties of these individual moieties.

SUBMITTER: Quinn S

PROVIDER: S-EPMC9783862 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Donor-Acceptor Dyads and Triads Employing Core-Substituted Naphthalene Diimides: A Synthetic and Spectro (Electrochemical) Study.

Quinn Samuel S Davies E Stephen ES Pearce Nicholas N Rosenberg Callum C Pfeiffer Constance R CR Orton Georgia R F GRF Champness Neil R NR

Molecules (Basel, Switzerland) 20221208 24

Donor-acceptor dyads and triads comprising core-substituted naphthalene diimide (NDI) chromophores and either phenothiazine or phenoxazine donors are described. Synthesis combined with electrochemical and spectroelectrochemical investigations facilitates characterisation of the various redox states of these molecules, confirming the ability to combine arrays of electron donating and accepting moieties into single species that retain the redox properties of these individual moieties. ...[more]

PMID: 36557805

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Project description:In order to develop new organic materials for optoelectronic applications, a fundamental understanding of the electronic properties of specific chromophore combinations must be realized. To that end, we report "model" acceptor (A)-acceptor' (A')-acceptor (A) triads in which the pendants (A') we selected are well-known components of organic optoelectronic applications. Our pendants are sandwiched between two dialkoxyphenazine (A) through an alkyne bond. The A' was systematically increased in electron-deficiency from benzothiadiazole (BTD-P) to naphthalene diimide with octyl (NDI-O-P) or ethylhexyl groups (NDI-EH-P) to perylene diimide with ethylhexyl (PTCDI-EH-P) to assess changes in the electronic properties of the resultant molecules. Characterizations were performed using both experimental and theoretical methods. From optical and cyclic voltammetry, we found that the electron deficiency of each pendant was directly correlated to the energy level of the lowest unoccupied molecular orbital (E LUMO). When examining the simple molecular orbital diagrams produced at the B3LYP/6-31G* level of theory, the LUMOs were, as expected, primarily localized on the more electron-deficient pendants. In terms of the energy level of the highest occupied molecular orbital (E HOMO), the numerical values obtained experimentally also correlated with values obtained computationally. Attempting to construct a simplified model that would explain these correlated values was not as readily apparent, given the disparate physical characteristics of these compounds. For example, BTD-P and NDI-O-P/NDI-EH-P achieved planarity when computationally optimized, but PTCDI-EH-P adapted a "buckled" geometry on the central PTCDI, consequently forcing the attached phenazines out-of-plane. The title compounds showed solvent polarity-dependent fluorescence, which is indicative of intramolecular charge transfer. In conjunction with our theoretical study, the current system can be viewed as an extension of donor-acceptor-donor systems. Thermal properties characterized by differential scanning calorimetry revealed that reversible phase transitions were only observed for BTD-P. In addition, BTD-P was found to be an efficient gelator in 1,1,1-trichloroethane and toluene. The other compounds in this study did not form gels in any of the solvents tested, which may have been a result of the alkyl groups on the pendants hampering the fibrillation process.

Dataset Information

Donor-Acceptor Dyads and Triads Employing Core-Substituted Naphthalene Diimides: A Synthetic and Spectro (Electrochemical) Study.

Publications

Donor-Acceptor Dyads and Triads Employing Core-Substituted Naphthalene Diimides: A Synthetic and Spectro (Electrochemical) Study.

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