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Chirality and spatially pre-organized multi-porphyrinoids

Chloé Sooambar

CNRS, LCC (Laboratoire de Chimie de, Coordination), 205 route de Narbonne, 31077 Toulouse, France

The author is also affiliated at: Université de Toulouse, UPS, INPT, 31077 Toulouse, France

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Vincent Troiani

CNRS, LCC (Laboratoire de Chimie de, Coordination), 205 route de Narbonne, 31077 Toulouse, France

The author is also affiliated at: Université de Toulouse, UPS, INPT, 31077 Toulouse, France

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Hongjin Qiu

CNRS, LCC (Laboratoire de Chimie de, Coordination), 205 route de Narbonne, 31077 Toulouse, France

The author is also affiliated at: Université de Toulouse, UPS, INPT, 31077 Toulouse, France

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Sunichi Fukuzumi

Department of Material and Life Science, Graduate School of Engineering, Osaka University, ALCA and SENTAN, Japan

The author is also affiliated at: Science and Technology Agency (JST), Suita, Osaka 565-0871, Japan, and Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Korea, and Faculty of Science and Technology, Meijo University, ALCA and SENTAN, Japan, Science and Technology Agency (JST), Nagoya, Aichi 468-8502, Japan

SPP full member in good standing

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Lucia Flamigni

Retired

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Régis Rein

CNRS, LCC (Laboratoire de Chimie de, Coordination), 205 route de Narbonne, 31077 Toulouse, France

The author is also affiliated at: Université de Toulouse, UPS, INPT, 31077 Toulouse, France

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Nathalie Solladié

CNRS, LCC (Laboratoire de Chimie de, Coordination), 205 route de Narbonne, 31077 Toulouse, France

E-mail Address: nathalie.solladie@lcc-toulouse.fr

Correspondence to: Nathalie Solladié, tel.: (+33)5-6133-3202, fax: (+33)5-6155-3003.

SPP full member in good standing

The author is also affiliated at: Université de Toulouse, UPS, INPT, 31077 Toulouse, France

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https://doi.org/10.1142/S1088424618500396Cited by:3 (Source: Crossref)

Abstract

We report herein that chiral and enantiopure compounds such nucleosides and peptides can pre-organize multi-porphyrinic systems and influence their properties. The first example given concerns star-shaped mutli-porphyrins with chiral and enantiopure nucleosidic linkers. If the configuration is indeed a star-shaped nanomolecule, it appears that the induced conformation is nothing as expected. The four peripheral Zn(II) porphyrins collapse over the free-base central one, inducing totally different photo-physical properties. Despite a minor expected light energy harvesting behavior, the principal capability of this system is to quench the collected light energy and convert it from radiative to non-radiative de-activation. The second example concerns polypeptides with pendant porphyrins. The peptidic backbone confers to the systems, after a certain degree of oligomerization, a 3 $_{10}$ $_{10}$ right handed helical conformation which induces cavities within the multi-porphyrinc architecture, ready to welcome guests and render, for example, the complexation of C $_{60}$ $_{60}$ much easier. We thus have constructed novel organic photovoltaic systems using supramolecular complexes of porphyrin–peptide oligomers with fullerene clusters. The composite cluster OTE/SnO $_{2}$ $_{2}$ electrode prepared with (P(ZnP) $_{16} +$ $_{16} +$ C $_{60})_{m}$ $_{60})_{m}$ , exhibits an impressive incident photon-to-photocurrent efficiency (IPCE) with values reaching as high as 56%. The power conversion efficiency of the (P(H $_{2}$ $_{2}$ P) $_{16} +$ $_{16} +$ C $_{60})_{m}$ $_{60})_{m}$ modified electrode reaches 1.6%, which is 40 times higher than the value (0.043%) of the porphyrin monomer (P(H $_{2}$ $_{2}$ P) $_{1}$ $_{1}$ $+$ $+$ C $_{60})_{m}$ $_{60})_{m}$ modified electrode. Thus, the organization approach between porphyrins and fullerenes with polypeptide structures is promising, and may make it possible to further improve the light energy conversion properties by using a larger number of porphyrins in a polypeptide unit.

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