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Department of Chemistry, University of Pavia LE GIORNATE DI CHIMICA ORGANICA A PAVIA Aula Magna, Palazzo Centrale dell’Università Wednesday, 15 th October 2014
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Page 1: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

Department of Chemistry, University of Pavia

LE GIORNATE DI CHIMICA ORGANICA A PAVIA

Aula Magna, Palazzo Centrale dell’Università

Wednesday, 15th October 2014

Page 2: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

Under the auspices of:

Sponsored by:

Page 3: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

Program

9.30

Opening Remarks

9.45

Shedding Light on Nanomedicine: Photoactivated Nanoconstructs

with Multiple Imaging and Therapeutic Modalities

Salvatore Sortino (University of Catania, Italy)

10.35

Organic and organometallic materials for new generation photovoltaic cells

Alessandro Abbotto (University Milano-Bicocca, Italy)

(11.25-11.50 break)

11.50

Photochromism of Diarylethene Molecules and Crystals

Masahiro Irie (Rikkyo University, Tokyo, Japan)

(lunch break)

14.30

Photoredox catalysis in Organic Synthesis

David MacMillan (Princeton University, USA)

Page 4: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

Shedding Light on Nanomedicine: Photoactivated Nanoconstructs with Multiple Imaging and Therapeutic Modalities

Salvatore Sortino

Laboratory of Photochemistry, Department of Drug Sciences, University of Catania,

Viale A. Doria 95125, Catania, Italy; [email protected]

The achievement of molecular nanoconstructs able to release multiple therapeutic species in a controlled fashion is a major challenge in the burgeoning field of nanomedicine (1). Light is a powerful tool for the introduction of bio-active agents in a cellular environment, mimicking an “optical microsyringe” with an exquisite control of three main factors, site, timing and dosage, which are determining for the therapeutic outcome (2). Moreover light-triggering is biofriendly and offers the additional advantages of not affecting important physiological parameters such as temperature, pH and ionic strength. In this context, the use of photoactive compounds having intrinsic fluorescence properties or their integration with suitable fluorogenic units is a fundamental requisite for an imaging-guided phototherapy. This allows indeed the visualization of the phototherapeutic agent in cells through fluorescence techniques and can provide a highly localized “burst” precisely at the desired sites. Singlet oxygen (1O2) and nitric oxide radical (NO) are able to attack biological substrates of different nature (i.e., lipids, proteins, and DNA) representing multitarget therapeutic agents and avoiding Multiple Drug Resistance problems encountered with several conventional drugs often target-specific. Due to their short half-life and lack of charge, both 1O2 and NO radical diffuse in the cellular environment over short distances without inflicting systemic side effects common to general anticancer drugs. For all these reasons, the combination of 1O2 with NO has received growing attention in the last few years (3) with the exciting prospect to tackle cancer and bacterial diseases. In our laboratories, we have been working on the design and fabrication of a number of nanoplatforms merging multicolor fluorescence imaging and multimodal therapeutic photofunctionalities. This contribution illustrates some of the most recent and representative examples including molecular and supramolecular conjugates, polymer nanoparticles, hydrogels and quantum dots, highlighting the rationale design and their potential relevance in biomedical research. (1) Komarova, N. L.; Boland, C. R. Nature 2013, 499, 291. (2) Sortino, S. J. Mater. Chem. 2012, 22, 301. (3) Sortino, S. Chem. Soc. Rev. 2010, 39, 2903.

1O2

•NO1O2

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Organic and organometallic materials for new generation photovoltaics (and solar fuels)

Alessandro Abbotto

Department of Materials Science and Solar Energy Center MIB-SOLAR,

University of Milano-Bicocca, Via Cozzi 55, Milano (I) [email protected]

Energy from Sun in modern society implies both electricity and fuels. With this target in mind we have developed in the last years a multidimensional approach, from molecular design to device, based on hybrid and organic materials. Our studies on organometallic and organic sensitizers, (1-3) iodine-free and quasi-solid electrolytes, (4) nanostructured TiO2 (5) will be presented. In particular we have introduced in the last years a new design approach for metal-free sensitizers, now widely used in the DSSC community, based on a multi-branched geometry, for improved light harvesting and enhanced stability compared to the conventional linear D--A sensitizers. (1) We will also present our most recent results on multi-branched dyes for solar-induced hydrogen production from water. In the last part of the lecture a few slides will be dedicated to the introduction of EnerCHEM, the recently established group of the Italian Chemical Society on Chemistry of Renewable Energies, whose members come for the diverse areas of research on renewable energy materials and devices in Italy. (6)

(1) Reviews: Manfredi, N.; Cecconi, B.; Abbotto, A. Eur. J. Org. Chem. 2014, DOI: 10.1002/ejoc.201402422; Abbotto, A.; Manfredi, N. Dalton Trans. 2011, 40, 12421. (2) Abbotto, A.; Coluccini, C.; Dell'Orto, E.; Manfredi, N.; Trifiletti, V.; Salamone, M. M.; Ruffo, R.; Acciarri, M.; Colombo, A.; Dragonetti, C.; Ordanini, S.; Roberto, D.; Valore, A. Dalton Trans. 2012, 41, 11731; Coluccini, C.; Manfredi, N.; Salamone, M. M.; Ruffo, R.; Lobello, M. G.; De Angelis, F.; Abbotto, A. J. Org. Chem. 2012, 77, 7945; Lobello, M. G.; Fantacci, S.; Manfredi, N.; Coluccini, C.; Abbotto, A.; Nazeeruddin, M. K.; De Angelis, F. Thin Solid Films 2014, 560, 86. (3) Abbotto, A.; Leandri, V.; Manfredi, N.; De Angelis, F.; Pastore, M.; Yum, J.-H.; Nazeeruddin, M. K.; Grätzel, M. Eur. J. Org. Chem. 2011, 2011, 6195; Leandri, V.; Ruffo, R.; Trifiletti, V.; Abbotto, A. Eur. J. Org. Chem. 2013, 2013, 6793; Di Carlo, G.; Biroli, A. O.; Pizzotti, M.; Tessore, F.; Trifiletti, V.; Ruffo, R.; Abbotto, A.; Amat, A.; De Angelis, F.; Mussini, P. R. Chem. Eur. J. 2013, 19, 10723. (4) Manfredi, N.; Bianchi, A.; Causin, V.; Ruffo, R.; Simonutti, R.; Abbotto, A. J. Polym. Sci. Part A 2014, 52, 719. (5) Trifiletti, V.; Ruffo, R.; Turrini, C.; Tassetti, D.; Brescia, R.; Di Fonzo, F.; Riccardi, C.; Abbotto, A. J. Mater. Chem. A 2013, 1, 11665; Dell'Orto, E.; Raimondo, L.; Sassella, A.; Abbotto, A. J. Mater. Chem. 2012, 22, 11364. (6) http://www.soc.chim.it/it/gruppi/enerchem/home.

Page 6: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

Photochromism of Diarylethene Molecules and Crystals

Masahiro Irie

Research Center for Smart Molecules, Rikkyo University, Tokyo, Japan [email protected]

Photochromism is defined as a reversible transformation of a chemical species between two isomers having different absorption spectra induced in one or both directions by photoirradiation. Although vast numbers of photochromic molecules have been so far reported, molecules which exhibit thermally irreversible photochromic reactivity are limited. A new class of thermally irreversible photochromic molecules is a “diarylethene” family. (1,2) The diarylethenes are derivatives of stilbene. When the phenyl rings of stilbene are replaced with five membered heterocyclic rings with low aromatic stabilization energy, both open- and closed-ring isomers become thermally stable. Diarylethenes undergo reversible cyclization and cycloreversion reactions in a picosecond time region upon alternate irradiation with UV and visible light and the coloration/decoloration cycles can be repeated more than 10,000 times. The chemical bond rearrangement induces electronic as well as geometrical structure changes. The electronic structure changes can be potentially applied to ultrahigh density (Pbits/inch2) optical memory media, (3), various photoswitching devices and super-resolution fluorescence imaging. (4) The geometrical structure changes can be applied to light-driven actuators and others (5-8). In this lecture, fundamental properties of diarylethene molecules and crystals, and their applications to photoswitchable fluorescence imaging and light-driven actuators will be presented. (1) Irie, M; Mohri, M. J. Org. Chem., 1988, 53, 803. (2) Irie, M. Chem. Rev. 2000, 100, 1685. (3) Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. Nature, 2002, 420, 759. (4) Uno, K.; Niikura, H.; Morimoto, M.; Ishibashi, Y.; Miyasaka, H.; Irie, M. J. Am. Chem. Soc., 2011, 133, 13558. (5) Irie, M.; Kobatake, S.; Horichi, M. Science, 2001, 291, 1769. (6) Kobatake, S.; Takami, S.; Muto, H.; Ishikawa, T.; Irie, M. Nature, 2007, 446, 778. (7) Morimoto, M.; Irie, M. J. Am. Chem. Soc., 2010, 132, 14172. (8) Terao, F.; Morimoto, M.; Irie, M. Ang. Chem. Int. Ed., 2012, 51, 901.

Page 7: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

Photoredox Catalysis: A Molecule Activation Strategy to Enable New Chemical Reactions

David W. C. MacMillan

Merck Center for Catalysis, Princeton University, Princeton, NJ 08544

[email protected]

This lecture will discuss the advent and development of new concepts in chemical synthesis, specifically the combination of photoredox catalysis with organic catalysis. This new approach to “synergistic catalysis” will demonstrate that multiple yet separate catalytic cycles can be aligned to generate activated intermediates that rapidly combine with each other, thereby allowing new approaches to enantioselective C-C and C-heteroatom bond formation. We will also introduce an approach to the discovery of new chemical reactions that we term accelerated serendipity. Accidental or ‘serendipitous’ discoveries have led to some of the most important breakthroughs in scientific history, many of which have directly affected human life. Given our overarching goal of developing fundamentally new and useful chemical transformations using catalysis and by acknowledging the tremendous impact of serendipity in scientific discovery, we questioned whether this phenomenon could be forced or simulated and therefore employed as a tool for reaction discovery. In this presentation, we will describe several new transformations that have been discovered in our laboratory that we expect will find widespread adoption throughout the field of chemical synthesis. Moreover, we will further describe how mechanistic understanding of these processes has led to the design of new yet fundamental chemical transformations. In particular: (i) a new catalysis activation mode that allows for the direct functionalization of ketones and aldehydes at the -carbon position, (ii) a new synergistic catalysis approach to C-H bond functionalization, and (iii) the development of decarboxylative coupling reactions.

Page 8: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

Last Editions

Page 9: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

LE GIORNATE DI CHIMICA ORGANICA A PAVIA

3 Ottobre 2013

[4+2] Cyclodditions: Vintage Reactions for New Glycomimetics

Cristina Nativi (University of Firenze)

Targeting Metabolic Nuclear Receptors: from the Ocean to theDiscovery of Novel Lead Compounds

Angela Zampella (University of Napoli)

Strategies and Tools for Activity-Based Protein profiling:

a Focus on Proteases and Glycosidases

Herman Overkleeft (Leiden University)

Page 10: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

LE GIORNATE DI CHIMICA ORGANICA A PAVIA

18 Maggio 2010

N-O Reagents and Catalysis in Heterocyclic Chemistry

The Rich Chemistry Stemming from N-O Cleavage of Strained Isoxazolines

Alberto Brandi (University of Firenze)

From Nitrile Oxides to Nitrosocarbonyls:

Chemical Behaviour and Synthetic Use

Paolo QuadreIli (University of Pavia)

Syntheses of Pentatomic Heterocycles as Viral Polymerase Inhibitors

Ugo Chiacchio (University of Catania)

Palladium Catalyzed Reactions as a Tool for the Synthesis of

Nitrogen-containing Heterocycles

Gianluigi Broggini (University of Insubria)

Modular Enhancement of Nature's Diversity (MEND):

Nitroso Diels-Alder and Ene Reactions in Syntheses and for Facile

Derivatization and Functionalization of Natural Products

Marvin J. Miller (University of Notre Dame, IN-USA)

Page 11: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

LE GIORNATE DI CHIMICA ORGANICA A PAVIA

27 Marzo 2009

Advanced Functional Nanomaterials:

Design, Synthesis and Applications

Cyclic Organic Molecules and Polymers: Towards Functional Nanomaterials

Dario Pasini (University of Pavia)

Self-Assembly of Molecular Materials via Halogen Bonding

Giuseppe Resnati (Politecnico di Milano)

Artificial Tongues and Leaves

Stefan Matile (University of Geneva, Switzerland)

Organic Functionalization of Carbon Nanotubes for

Applications in Materials Science and Nanomedicine

Maurizio Prato (University of Trieste)

Functional Polymers: from Catalytic Nanoreactors

to Energy Materials and Therapeutic Carriers

Jean M. J. Fréchet (University of California, Berkeley, USA)

Page 12: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

LE GIORNATE DI CHIMICA ORGANICA A PAVIA

9 Aprile 2008

Controllare Reattività e Selettività:

dall'Effetto Solvente all'Organocatalisi

Catalysis of Organic Reactions in Water and under Solvet-Free Conditions

Francesco Fringuelli (University of Perugia)

Solvents, Salts, Asymmetric Catalysis: a Long Journey

Giuseppe Faita (University of Pavia)

Atropoisomeric Ligands with Phosphorus Donors. A Never-ending Story

Serafino Gladiali (University of Sassari)

Ligand Libraries for Enantioselective Catalysis

Cesare Gennari (University of Milano)

Organocatalysis - After the Goldrush

Karl Anker Jørgensen (Aarhus University, Denmark)

Page 13: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

LE GIORNATE DI CHIMICA ORGANICA A PAVIA

18 Maggio 2007

Attualità delle Ricerche sui Metaboliti Secondari:

Domande dalla Biologia; Risposte dalla Chimica

La Natura come Fonte e Ispirazione di Collezioni di Composti Bioattivi:

Studi sui Terpenoidi Marini Inibitori delle sPLA2

Raffaello Riccio (University of Salerno)

Prenilossiderivati di Fenilpropanoidi

Massimo Curini (University of Perugia)

I Composti Naturali come Sonde Molecolari per Esplorare la Complessità

Biologica: la Lezione della Lipodomica

Giovanni Appendino (University of Piemonte Orientale e Novara)

Lo Stress Ossidativo: Aspetti Chimici e Biologici

Giuseppe Zanoni (University of Pavia)

Amphotericin B: Chemical and Biological Studies

Erick M. Carreira (ETH Zürich, Switzerland)

Page 14: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

LE GIORNATE DI CHIMICA ORGANICA A PAVIA

3 Maggio 2006

Verso una Chimica Ecocompatibile

Zeolite based Photocatalysis

Hermengildo Garcia (UPV Valencia, Spain)

Green Chemistry nell'Industria Farmaceutica

Walter Cabri (Antibioticos)

L'Organizzazione Strutturale dei Liquidi Ionici e le loro Proprietà Solvente

nelle Reazioni Organiche e nei Processi Catalizzati

Cinzia Chiappe (University of Pisa)

Arilazione Fotochimica come Alternativa alle Reazioni Mediate da Metalli

Maurizio Fagnoni (University of Pavia)

From Chirality Transfer to Chirality Multiplication. Hydrogen Bond-mediated

Enantioselectivity of Photochemical Reactions in Solution

Thorsten Bach (TUM München, Germany)

Page 15: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

LE GIORNATE DI CHIMICA ORGANICA A PAVIA

6 Ottobre 2005

Chemistry in Action on DNA.

Molecular Aspects of the Damage and Repair

Customized Fused Aromatics for Structural Recognition of Nucleic Acids

Marie-Paule Teulade-Fichou (Collège de France, Paris, France)

DNA Changes in Development and the Paucity of Human Genes

Vittorio Sgaramella (CERSA/Parco Tecnologico Padano, Lodi)

Generazione e Reattività di Alchilanti e di Agenti di "Cross-Linking".

Un approccio Sperimentale e Computazionale

Mauro Freccero (University of Pavia)

Acidi Nucleici: Farmaci e Target Farmacologici

Manlio Palumbo (University of Padova)

Predicting and Controlling Selective Alkylation of DNA

Steven E. Rokita (University of Maryland, College Park, USA)

Page 16: LE GIORNATE DI CHIMICA ORGANICA A PAVIA · Self-Assembly of Molecular Materials via Halogen Bonding Giuseppe Resnati (Politecnico di Milano) Artificial Tongues and Leaves Stefan Matile

Da “ARS SIVE DOCTRINA DE TRASMUTATIONE METALLORUM”

anno 1462 - Biblioteca Universitaria - Pavia


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