Molecules for organic electronics: intermolecular interactions vs properties
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1 Molecules for organic electronics: intermolecular interactions vs properties Chiara Bertarelli Dipartimento di Chimica, Materiali e Ing. Chimica G. Natta Politecnico di Milano chiara.bertarelli@polimi.it website: tel
2 Basic ingredients of molecules for organic electronics keleton Alkyl chains Functional groups X COOH OMe CN
3 Intermolecular interactions keleton Offset stacking p stacking X T-stacking Aromatic-aromatic interaction (aromatic stacking, pi stacking): A noncovalent attractive force between two aromatic rings. Alignment of positive electrostatic potential on one ring with negative electrostatic potential on another ring forms: an offset stack, or a T-shaped stack. Also called pi stacking but this label is misleading because it implies that stacking might occur in any structure with pi electrons.
4 Intermolecular interactions: p stacking keleton X p stacking Electrical anisotropy tacked base pairs cause aromatic-aromatic interactions in DNA
5 Intermolecular interactions: p stacking keleton X p stacking Electrical anisotropy Generally speaking, pi-stacking offers a preferential path for the carriers, thus increasing mobility. Acenes, and in particular pentacene and derivatives, have been extensively studied in organic transistors. Acenes
6 porphyrins
7 Intermolecular interactions: p stacking TTF NC NC CN CN TCNQ
8 Intermolecular interactions: Van der Waals Alkyl chains Van der Waals Weak secondary bond trong effect in intermolecular packing hort range interaction chematic illustrations for (a) the packing structure of PQT (P2) and PBTTT (P3) with dodecyl side chain with uniform side chain interdigitation and (b) proposed packing structure for P30 with disordered side chains. Reprinted with permission from ref 52. Copyright 2009 American Chemical ociety.
9 Intermolecular interactions: Van der Waals Alkyl chains Van der Waals Weak secondary bond trong effect in intermolecular packing hort range interaction Example #1: amphiphiles HO O stearic acid Polar head Apolar tail
10 Intermolecular interactions: Van der Waals Alkyl chains Van der Waals Weak secondary bond trong effect in intermolecular packing hort range interaction Example #2: AMs (self-assembled monolayers) A self-assembled monolayer (AM) is an organized molecular assembly formed spontaneously by the adsorption (absorption) of a surfactant onto a solid surface. The major driving forces governing AM formation are the relative strength of the: -ubstrate-surfactant (head group) interaction, -urfactant-surfactant interaction -urfactant solvent interaction
11 AMs (self-assembled monolayers): alkanethiols onto gold Upon immersion of a clean gold surface into a dilute solution (typically 1mM) of an alkanethiol derivative, the thiol molecules are chemisorbed via the formation of dative gold-sulfur bonds. - Gold has specific interaction with sulfur - Long-chain alkanethiols form densely packed, crystalline or liquid-crystalline monolayers due to strong molecular interactions (van der Waals forces) between long carbon chains. H
12 Mixed AMs (self-assembled monolayers): alkanethiols onto gold using two or more alkanethiols, mixed monolayers can be formed. the composition of the mixed AMs differs from the composition of the solution and depends on the tendency of each surfactant to form densely packed films bulky tail groups or functionalized with strong polar groups can prevent their insertion in AM growth, as they disturb the Van der Waals interaction
13 #3: Alkyl chains onto well-packed aromatic moieties: liquid crystals Liquid crystals are examples of self-assembling structures, as a result of intermolecular interactions: ECONDARY TRUCTURE These structures are characterized by a some degree of long-range molecular order. The particular intermolecular interactions define the specific secondary structure, that is the liquid crystal phase. Liquid crystals are fluid, so they form continuous structures without interfaces. Liquid crystal phases differ from a liquid phase due to the peculiar anisotropy R= long alkyl (or perfluorinated alkyl) chain
14 Adding a strong polar group: large dipole moment n = F O F F O O F C 3 H 7 econdary structure Tertiary structure
15 Intermolecular interactions Functional groups COOH OMe CN Hydrogen bonding Dipole-dipole interaction
16 Intermolecular interactions Functional groups COOH OMe CN Hydrogen bonding Dipole-dipole interaction A noncovalent (van der Waals) attractive force caused by alignment of bond dipoles with opposite charges.
17 Intermolecular interactions Functional groups COOH OMe Hydrogen bonding A non covalent attractive force caused by electrostatic attraction of a hydrogen atom with a lone pair of another atom. The hydrogen bond donor must have a sufficiently large d+ charge caused by bonding to a highly electronegative element (O, N, or F). The hydrogen bond acceptor must have a lone pair, and sufficiently high electron density. CN water
18 upramolecular organization J.-M. Lehn, Chem. Eur. J. 2007, 13,
19 From solid state to solution: solubility solubilization: the structural units (ions or molecules) gets separated energy has to be provided to overcome the interionic or intermolecular forces energy required to break the bonds between particles is recovered by formation of new bonds between solute and solvents molecules the variation of entropy due to solubilization is positive (as disorder increases)
20 From solid state to solution: solubility energy required to break the bonds between particles is recovered by formation of new bonds between solute and solvents molecules the variation of entropy due to solubilization is positive (as disorder increases)
21 From solid state to solution: solubility Main statement: similar likes similar ubstance: methane d + d H H + C H d + d + H d - olubility in water: zero olubility in CCl 4 : high NaCl olubility in water: high olubility in CCl 4 : zero
22 From solid state to solution: solubility d + d + H d - H O olubility of alcohols into water Alcohol CH 3 OH CH 3 OH CH 3 OH CH 3 OH CH 3 OH CH 3 OH CH 3 OH solubility g/100g H 2 O CH 3 OH 0.05
23 olubility: amphiphiles if molecules are large enough and bear an apolar moiety and a polar group, this double nature influences solubilization, thus showing an amphiphilic behaviour pherical micelle Crosssection Rod micelle close-up odio laurato
24 olubility: amphiphiles aggregates are thus formed (es. micelle) whose shape is determined by the specific structure of the amphiphile, on its concentration and on temperature micelles are on the basis of cleaning
25 olubility: the conjugated systems solubility is usually a basic requirement to process materials into thin films by means of easy-handling solution techniques (spin coating, casting). At the solid state, conjugated systems and specifically oligo- /poly-aromatic systems are characterized by interactions p-p the longer the oligomer, the poorer the solubility T 2T 3T 4T 5T 6T
26 olubility: the conjugated systems the use of polar solvents having relatively high dielectric constant, but with no acid proton, can favour solubilization of conjugated systems aromatic solvents can contribute to solubilization as they can interact trough the p electronic cloud (entropy is relevant) O O C H 3 C CH H N CH 3 3 CH 3 (CH 3 ) 2 N O P N(CH 3 ) 2 N(CH 3 ) 2 dimetilsolfossido (DMO) N,N-dimetilformamide (DMF) esametilfosforotriammide (HMPT) CH 3 Cl Cl toluene o-diclorobenzene in case of planar systems and with very effective p stacking mixture of different solvent can help in solubilizing. trong acids plus aprotic solvents with high dielectric constant are typical examples
27 olubility of the conjugated systems: The effect of alkyl chains Alkyl chains are characterized by high conformational freedom their electronic effect on conjugation is very weak (weak donor) Usually they force a distortion of inter ring bonds (ateric hindrance) if they are placed in a regular way, crystallinity is favoured
28 olubility of the conjugated systems: The effect of alkyl chains R R R R R R CORONENE EABENZOCORONENE EABENZOCORONENE R=C12H25 C60 R R R C114 C132 C222 R R CORONENE: OLUBLE IN ACETONE, TOLUENE, CLOROFORM C78 R R R C60 R=C12H25 HEXABENZOCORONENE: ALMOT INOLUBLE UBTITUTED HEXABENZOCORONENE: OLUBLE IN CLOROFORM C60,78,114,132,222: INOLUBLE UBTITUTED C60 : OLUBLE IN CLOROFORM
29 solvatochromism solvatochromic and/or thermochromic phenomena are commonly occurring in conjugated systems these phenomena are often related to the formation of aggregates (p-stacking) which occurs in presence of bad solvents or in mixtures of good and bad solvents techniques: light scattering, circular dichroism, UV-vis absorption spectra, photoluminescence, microfiltration, etc.
30 solvatochromism polymer OMe * n * regioregularity: % M n : solvents Bad solvent: MeOH M. Lanzi, P. Costa-Bizzarri, C. Della Casa, ynth Metals, 89 (1997) 181
31 solvatochromism Yellow-orange dioxane Red-purple toluene MeOH MeOH polar solvent site of solvatation: end group Non-solvent effect: relatively high less polar solvent site of solvatation: backbone Non-solvent effect: weak (at low molar concentration) M. Lanzi, P. Costa-Bizzarri, C. Della Casa, ynth Metals, 89 (1997) 181
32 solvatochromism/thermochromism OH polymer * n * regioregularity: 75% M n : solvents solubility Bad solvent: MeOH F. Bertinelli, P. Costa-Bizzarri, C. Della Casa, M. Lanzi, ynth Metals, 122 (2001) 267
33 solvatochromism MeOH F. Bertinelli, P. Costa-Bizzarri, C. Della Casa, M. Lanzi, ynth Metals, 122 (2001) 267
34 thermochromism giallo-arancio rosso-viola 18 C -62 C
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