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Journal of Materials Chemistry C Volume 3 Number 4 28 January 2015 Pages 705–900 Journal of Materials Chemistry C Materials for optical, magnetic and electronic devices www.rsc.org/MaterialsC ISSN 2050-7526 PAPER Alessandra Forni, Giuseppe Resnati, Pierangelo Metrangolo, Arri Priimagi et al. Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning Journal of Materials Chemistry C View Article Online PAPER View Journal | View Issue Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface Cite this: J. Mater. Chem. C,2015,3, 759 patterning† Marco Saccone,a Valentina Dichiarante,b Alessandra Forni,*c Alexis Goulet- Hanssens,‡d Gabriella Cavallo,b Jaana Vapaavuori,§a Giancarlo Terraneo,b Christopher J. Barrett,d Giuseppe Resnati,*b Pierangelo Metrangolo*be and Arri Priimagi*abf Halogen bonding, a noncovalent interaction possessing several unique features compared to the more familiar hydrogen bonding, is emerging as a powerful tool in functional materials design. Herein, we unambiguously show that one of these characteristic features, namely high directionality, renders halogen bonding the interaction of choice when developing azobenzene-containing supramolecular polymers for light-induced surface patterning. The study is conducted by using an extensive library of Creative Commons Attribution 3.0 Unported Licence. azobenzene molecules that differ only in terms of the bond-donor unit. We introduce a new tetrafluorophenol-containing azobenzene photoswitch capable of forming strong hydrogen bonds, and Received 14th October 2014 show that an iodoethynyl-containing azobenzene comes out on top of the supramolecular hierarchy to Accepted 21st November 2014 provide unprecedented photoinduced surface patterning efficiency. Specifically, the iodoethynyl motif DOI: 10.1039/c4tc02315c seems highly promising in future development of polymeric optical and photoactive materials driven by www.rsc.org/MaterialsC halogen bonding. Introduction rod-like trans-form and a bent cis-form,2 which can give rise to a This article is licensed under a cascade of motions beyond the size scale of an individual The azobenzene moiety is an important tool in present-day molecule. When the azobenzene is incorporated into a liquid- research of molecular-level photoswitching and is extensively crystalline or a polymeric medium, the photoisomerization can used for the development of macroscopic photonic and photo- accomplish various tasks, allowing for induction of order– Open Access Article. Published on 25 November 2014. Downloaded 9/28/2021 1:33:43 PM. mechanical materials.1 The interest in azobenzene lies in its disorder transitions, control over the molecular alignment, clean, efficient, and reversible photoisomerization between a photoactuation of the shape and dimensions of the material system, and inscription of surface-relief patterns onto thin azobenzene-containing lms.3 In particular, when an azo- aDepartment of Applied Physics, Aalto University, P.O. Box 13500, FI-00076 Aalto, benzene-containing thin polymer lm is irradiated with a Finland polarization/intensity interference pattern of light, the lm bNFMLab-DCMIC “Giulio Natta”, Politecnico di Milano, Via L. Mancinelli 7, IT-20131 surface deforms and creates a replica of the incident interfer- Milano, Italy. E-mail: [email protected]; [email protected] cISTM-CNR, Institute of Molecular Sciences and Technologies of CNR, Universita` degli ence pattern in the form of a surface topography pattern, o en 4 Studi di Milano, Via Golgi 33, IT-20133 Milano, Italy. E-mail: alessandra.forni@istm. denoted as a surface-relief grating (SRG). The modulation cnr.it depth of the photoinduced surface patterns can be hundreds of dDepartment of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, nanometers, creating efficient diffractive optical elements with Quebec H3A 0B8, Canada a rst-order diffraction efficiency of up to 30–40%. SRGs have e VTT-Technical Research Centre of Finland, P.O. Box 1000, FI-02044 VTT, Finland been used as nanostructuring tools, liquid-crystal alignment fDepartment of Chemistry and Bioengineering, Tampere University of Technology, P. O. layers, and periodic light trapping/light outcoupling layers.5 Box 541, FI-33101 Tampere, Finland. E-mail: arri.priimagi@tut. † Electronic supplementary information (ESI) available: Synthesis procedures and Despite their application potential, however, the surface pattern compound characterization, computational details, description of photochemical formation mechanism is not yet well understood. Therefore, a experiments, and crystal data. CCDC 1025655 and 1025656. For ESI and full understanding of structure–function relationships that crystallographic data in CIF or other electronic format see DOI: govern the SRG process is needed in order to design better 10.1039/c4tc02315c performing materials for future advanced applications. ‡ Present address: Department of Chemistry, Humboldt-Universit¨at zu Berlin, Supramolecular side-chain polymers, in which the photo- Brook-Taylor-Str. 2, 12489 Berlin, Germany. § Present address: D´epartement de Chimie, Universit´e de Montr´eal, Montr´eal, QC, active azobenzene units are attached to a passive polymer Canada H3C 3J7. backbone via noncovalent interactions, have in the past few This journal is © The Royal Society of Chemistry 2015 J. Mater. Chem. C,2015,3,759–768 | 759 View Article Online Journal of Materials Chemistry C Paper years emerged as a new class of SRG-forming materials.6 The Results and discussion importance of these materials lies in their extreme ease of preparation and modular tunability: the material composition Materials design can be easily optimized to meet specic requirements. As a The library of azobenzene compounds shown in Fig. 1 allows for result, high-quality resonance lters, and patterns with record- (i) establishing an optimal halogen-bond donor in terms of SRG high modulation depth have been fabricated from azobenzene- formation capability, and (ii) comparing structurally similar containing supramolecular side-chain polymers.6a,7 We have azobenzenes substituted with halogen-bond versus hydrogen- recently shown that halogen bonding8 appears particularly bond donor groups. The series of peruorinated azobenzenes promising for the design of supramolecular SRG-forming 1–5 comprises a reference molecule incapable of forming materials.9 Halogen bonding is the noncovalent interaction in halogen bonds (1), two halogen-bond donors (2, 3) with similar which a region of positive electrostatic potential on top of the spectral and photochemical properties but different interaction surface of the halogen atom, the s-hole,10 interacts with a strengths (Br < I), and two hydrogen-bond donors, one weak (4) nucleophilic site. High-level ab initio quantum-chemical calcu- and one strong peruorophenol-containing dye (5). Compound lations suggest that dispersion forces may also play an impor- 5 serves a dual purpose. Firstly, a close structural relationship tant role in this interaction.11 The features that distinguish with 3 affords an ideal comparison for halogen bonding versus halogen bonding from hydrogen bonding are of particular hydrogen bonding in driving the SRG formation process. interest, which include higher directionality, hydrophobicity, Secondly, the peruorinated phenol presumably acts as a very size of the interacting atom (halogen vs. hydrogen) and the powerful hydrogen-bond donor and could therefore give rise to possibility to tune interaction strength by a simple change of a very strong noncovalent interaction,17,18 which is interesting in the halogen atom.12 These characteristic properties have its own right in the eld of functional supramolecular mate- allowed for the ne tuning of geometrical features relevant to rials. This is the rationale for the comparison between 5 and its crystal engineering13 and to the design of functional materials nonuorinated counterpart 7, the SRG performance of which is 14 15 9 Creative Commons Attribution 3.0 Unported Licence. with unique light-emissive and liquid-crystalline properties. known. Recently several examples of halogen-bonded supramolec- The non-uorinated dyes 6–9 include the already mentioned ular structures involving azobenzenes have been reported.9,16 phenol-substituted compound 7, an iodo-substituted azo- For example, we showed that the efficiency of SRG formation benzene 6 that is expected to act as a weak halogen-bond donor, increases with the strength of halogen bonding, and that the and ethynyl-substituted dyes 8 and 9. The latter two compounds high performance of halogen-bonded complexes seems to be are particularly interesting, since very recently iodoethynyl- connected more to the directionality of halogen bonding than benzenes were investigated both theoretically and experimen- to its intrinsic interaction strength. To further develop the tally with the purpose of establishing a hierarchy among practical applications of halogen bonding in the eld of pho- halogen-bond donors in crystal engineering.19 Based on ATR- This article is licensed under a tocontrollable materials, we have undertaken a detailed study FTIR and single crystal X-ray diffraction data, Aakeroy¨ et al. on the relative surface patterning efficiency that can be impar- proved that the iodoethynyl benzenes form co-crystals with a ted by different halogen-bond donors as a result of the presence larger class of halogen-bond acceptors compared to per- of electron-withdrawing substituents versus the hybridization of uoroiodobenzenes
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