2014
DOI: 10.1021/ja5015053
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Cooperatively Assembling Donor–Acceptor Superstructures Direct Energy Into an Emergent Charge Separated State

Abstract: A novel supramolecular system composed of diketopyrrolopyrrole electron donors and perylene derived bisimide (PDI) electron acceptors forms superstructures that undergo fast photoinduced charge separation following assembly. This bioinspired route toward functional hierarchical structures, whereby assembly and electronic properties are closely coupled, could lead to new materials for artificial photosynthesis and organic electronics.

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Cited by 84 publications
(108 citation statements)
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“…[12][13][14][15][16][17][18] In particular, self-organization of electron donor (D) and acceptor (A) moieties into highly ordered molecular architectures is extremely promising for organic solar cell applications. [19][20][21][22][23][24] Possible control of the energy and the charge transfer processes together with the existence of percolation pathways for both holes and electrons via the formation of well-dened, nanosegregated donoracceptor domains are indeed of critical importance for enhancing photovoltaic performances. Among the variety of LC donor-acceptor (D-A) materials developed so far, [25][26][27][28] covalently linked electron D-A dyad and triad molecules are of interest as their self-assembly can produce highly ordered wellseparated structures of well-stacked D and A p-molecules.…”
Section: Introductionmentioning
confidence: 99%
“…[12][13][14][15][16][17][18] In particular, self-organization of electron donor (D) and acceptor (A) moieties into highly ordered molecular architectures is extremely promising for organic solar cell applications. [19][20][21][22][23][24] Possible control of the energy and the charge transfer processes together with the existence of percolation pathways for both holes and electrons via the formation of well-dened, nanosegregated donoracceptor domains are indeed of critical importance for enhancing photovoltaic performances. Among the variety of LC donor-acceptor (D-A) materials developed so far, [25][26][27][28] covalently linked electron D-A dyad and triad molecules are of interest as their self-assembly can produce highly ordered wellseparated structures of well-stacked D and A p-molecules.…”
Section: Introductionmentioning
confidence: 99%
“…[11][12][13][14] Meanwhile, slipped-stackinginduced J-aggregate of the widely-used fluorophores has been mostly achieved by adsorption on the surface such as glass or zeolite. [15][16][17][18][19] Compared to porphyrin, perylene diimide, and cyanine derivatives that many rational molecular designs have been introduced to induce various aggregation, [20][21][22][23][24][25] there have been limited reports to control self-assembly of fluorophores in solution without a help of external templates. In this study, we aimed to develop a method to facilitate a Jaggregate formation of fluorophore by substituting a simple chemical group.…”
mentioning
confidence: 99%
“…To compare the photoinduced charge transfer processes of the mDPP-PDI films to those previously reported 28,29 for solution aggregates, a brief description of the femtosecond (fs) and nanosecond (ns) transient absorption (TA) on the individual compounds and on the 2:1 mDPP:PDI mixture in toluene is provided. Photoexcitation of solutions of mDPP and PDI in toluene ( Figure S26A,B), results in the appearance of ground state bleaching from 523−594 nm with corresponding positive The Journal of Physical Chemistry C Article excited states features between 700 and 800 nm and lifetimes around 2−5 ns.…”
Section: ■ Transient Absorption Spectroscopymentioning
confidence: 99%
“…The 1 *PDI deactivates multiexponentially, with lifetimes contributions of ∼1 ps (72%), assigned to excited state annihilation, 41 ps (15%), and a long-lived component >6 ns that are similar to previously reported excited state absorption decays of other PDIcontaining films. 29,43 The mDPP films that were photoexcited at 500 nm produce 1 *mDPP features at 450 nm and follow identical multiexponential decays, with average lifetimes of ∼3 ps (37%), 48 ps (35%), and 306 ps (26%) and a measurable long-lived component that persists on the nanosecond and microsecond time scales (Table S4). The multiexponential decay of the ∼2 ps component can be rationalized by 1 *mDPP annihilation, whose contribution decreases with decreasing pump energies ( Figure S30).…”
Section: ■ Transient Absorption Spectroscopymentioning
confidence: 99%