Polyimide Dendrimers Containing Multiple Electron Donor–Acceptor Units and Their Unique Photophysical Properties

Toma, Francesca M.; Puntoriero, Fausto; Pho, Toan V.; Rosa, Marcello La; Jun, Young‐Si; Villers, Bertrand J. Tremolet de; Pavlovich, J.; Stucky, Galen D.; Campagna, Sebastiano; Wudl, Fred

doi:10.1002/ange.201501298

Angewandte Chemie

2015

DOI: 10.1002/ange.201501298

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Polyimide Dendrimers Containing Multiple Electron Donor–Acceptor Units and Their Unique Photophysical Properties

Francesca M. Toma

Fausto Puntoriero²,

Toan V. Pho

et al.

Abstract: Ah igh-yielding synthesis of as eries of polyimide dendrimers,i ncluding decacyclene-and perylene-containing dendrimer D6,i nw hich two types of polyimide dyes are present, is reported. In these constructs,t he branching unit is represented by trisphenylamine,and the solubilizing chains by N-9-heptadecanyl-substituted perylene diimides.T he photophysical properties of the dendrimers have been studied by absorption, steady-state,a nd time-resolved emission spectroscopya nd pump-probe transient absorption spectr… Show more

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Cited by 3 publications

References 27 publications

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Kreisförmiger lichtinduzierter Elektronentransfer in einer Donor‐ Akzeptor‐Akzeptor‐Triade

Larsen¹,

Wenger²

2017

Angewandte Chemie

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Herein is communicated an electron donor-acceptoracceptor (D-A1-A2) triad that provides the first proof-of-concept for a photoinitiated molecular circuit. Upon photoexcitation into an optical charge-transfer transition between D and A1, subsequent thermal electron-transfer from A1to A2 is followed by geometric rearrangement in the D + -A1-A2charge-separated state to form an ionpair contact. This facilitates 'forward' charge-recombination between A2and D + that completes the molecular circuit, with an estimated quantum efficiency of 4% in toluene at 298 K.[a]

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Kreisförmiger lichtinduzierter Elektronentransfer in einer Donor‐ Akzeptor‐Akzeptor‐Triade

Larsen¹,

Wenger²

2017

Angewandte Chemie

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Circular Photoinduced Electron Transfer in a Donor‐Acceptor‐Acceptor Triad

Larsen

Wenger

2017

Angew Chem Int Ed

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An electron-donor-acceptor-acceptor (D-A -A ) triad has been developed that provides the first proof-of-concept for a photoinitiated molecular circuit. After photoexcitation into an optical charge-transfer transition between D and A , subsequent thermal electron-transfer from A to A is followed by geometric rearrangement in the D -A -A charge-separated state to form an ion-pair contact. This facilitates "forward" charge recombination between A and D to complete the molecular circuit with an estimated quantum efficiency of 4 % in toluene at 298 K.

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Synthesis and Properties of a Decacyclene Monoimide and a Naphthalimide Derivative as Three‐Dimensional Acceptor–Donor–Acceptor Systems

Yamamoto

Yoshida

Morii

et al. 2018

Chemistry An Asian Journal

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A method involving the Diels-Alder (DA) cycloaddition of diacenaphtheno[1,2-b;1',2'-d]thiophenes (DATs) with N-alkylacenaphthylene-5,6-dicarboximides (AIs) was developed to synthesize decacyclene monoimides (DCMIs). The reactions generate the corresponding 1:2 adducts (BAIAs) as major products together with 1:1 adducts (the DCMIs). The molecular structure of BAIAb (N-octyl derivative) was unambiguously assigned as the bis-adduct having an endo,endo spatial disposition of the two acenaphthylene-5,6-dicarboximide moieties by using X-ray crystallographic analysis. Relative to the absorption spectrum of decacyclene triimide (DCTIa, N-2-ethylhexyl derivative), that of the analogous N-2-ethylhexyl-substituted monoadduct, DCMIa, is bathochromically shifted despite the fact that it possesses a less delocalized π-electron system. DCMIa does not fluoresce in various organic solvents, whereas DCTIa emits yellow fluorescence in CH Cl with a low quantum yield (Φ ). Moreover, DCMIa in CDCl displays concentration-dependent H NMR spectroscopy behavior, which suggests that it self-aggregates with an association constant (K ) of (193±50) m at 20 °C. Despite the presence of four bulky tert-butyl groups in DCMIa, its K value for aggregate formation is comparable to that of DCTIa [(495±42) m ], which does not contain tert-butyl substituents. Spectroscopic studies with the bis-adduct BAIAa (N-2-ethylhexyl derivative) show that it displays remarkable solvatofluorochromism corresponding to an emission maximum shift (Δλ ) of 100 nm. The results of density functional theory calculations on BAIAc (N-methyl derivative) demonstrate that a considerable spatial separation exists between the HOMO and LUMO coefficient distributions, which indicates that the ground-to-excited state transition of the novel three-dimensional acceptor-donor-acceptor BAIAa system should have intramolecular charge-transfer character.

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Polyimide Dendrimers Containing Multiple Electron Donor–Acceptor Units and Their Unique Photophysical Properties

Cited by 3 publications

References 27 publications

Kreisförmiger lichtinduzierter Elektronentransfer in einer Donor‐ Akzeptor‐Akzeptor‐Triade

Kreisförmiger lichtinduzierter Elektronentransfer in einer Donor‐ Akzeptor‐Akzeptor‐Triade

Circular Photoinduced Electron Transfer in a Donor‐Acceptor‐Acceptor Triad

Synthesis and Properties of a Decacyclene Monoimide and a Naphthalimide Derivative as Three‐Dimensional Acceptor–Donor–Acceptor Systems

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