Usta, Hakan
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HAKAN USTA & Usta, H. & Usta, Hakan
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Prof. Dr.
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hakan.usta@agu.edu.tr
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02.07. Malzeme Bilimi ve Nanoteknoloji Mühendisliği
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2ZERO HUNGER
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3GOOD HEALTH AND WELL-BEING
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4QUALITY EDUCATION
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9INDUSTRY, INNOVATION AND INFRASTRUCTURE
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Documents
81
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6071
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34
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83
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5849
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Scholarly Output
77
Articles
53
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819/537
Supervised MSc Theses
2
Supervised PhD Theses
5
WoS Citation Count
2197
Scopus Citation Count
2297
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0
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2
WoS Citations per Publication
28.53
Scopus Citations per Publication
29.83
Open Access Source
23
Supervised Theses
7
| Journal | Count |
|---|---|
| Journal of Materials Chemistry C | 8 |
| ACS Applied Materials & Interfaces | 6 |
| Advanced Functional Materials | 3 |
| Synthetic Metals | 3 |
| Chemistry of Materials | 3 |
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Article Citation - Scopus: 1Labyrinthine Microstructures With a High Dipole Moment Boron Complex for Molecular Physically Unclonable Functions(American Chemical Society, 2025-10-29) Yıldız, T.A.; Kiremitler, N.B.; Kayacı, N.; Kalay, M.; Özcan, E.; Deneme, I.; Usta, H.The design and development of novel molecular-physically unclonable functions (PUFs) with advanced encoding characteristics and ease of fabrication have recently attracted attention in cryptography, secure authentication, and anticounterfeiting. Here, we report the development of a new high dipole-moment small molecule, InIm-BF<inf>2</inf>, a difluoroborate complex of an indolyl-imine ligand, and the fabrication of unique labyrinthine patterns through a facile two-step thin film process under ambient conditions. The new molecule has a dipolar, coplanar π-backbone and arranges in the solid state with antisymmetric cofacial π-stackings (3.86 Å). These properties, along with short C–H···π contacts (2.74–2.88 Å) and nonclassical C–H···F hydrogen bonds (2.47–2.51 Å) (23.4% and 11.5% of the Hirshfeld surfaces, respectively), drive the formation of amorphous molecular PUF patterns with disordered, short-range interactions. Spin-coating followed by thermal annealing at a moderate temperature produces nanoscopic molecular thin films with intricate labyrinthine patterns. These patterns, characterized by interconnected, irregularly shaped, micron-sized (≈50–100 μm) features, exhibit excellent PUF characteristics, verified through advanced image analysis and computational algorithms. Unlike randomly positioned isolated features in classical binarized keys, the interconnected labyrinthine patterns possess rich entropy and complex features, directly authenticated via deep-learning methodologies. Our work not only demonstrates a facile, promising approach to fabricating unique high-entropy PUF patterns but also provides critical insights into designing advanced molecular materials for next-generation security applications. © 2025 The Authors. Published by American Chemical SocietyDoctoral Thesis FUNCTIONALIZED LOW LUMO [1]BENZOTHIENO[3,2-B][1]BENZOTHIOPHENE (BTBT)-BASED MOLECULAR SEMICONDUCTORS FOR ORGANIC FIELD EFFECT TRANSISTORS(Abdullah Gül Üniversitesi, Fen Bilimleri Enstitüsü, 2021) Özdemir, Resul; Usta, HakanDAcTTs have provided an excellent π-framework for the development of high mobility p-type molecular semiconductors in the past decade. However, n-type DAcTTs are rare and their electron transporting characteristics remain largely unexplored. In the second chapter of this thesis, the first example of an n-type BTBT-based semiconductor, D(PhFCO)-BTBT, has been realized via a two-step transition metal-free process without using chromatographic purification. The corresponding TC/BG-OFET devices demonstrated μe (max) = ~0.6 cm2/Vs and Ion/Ioff ratio = 107-108. The large band-gap BTBT π-core is a promising candidate for high mobility n-type organic semiconductors and, combination of very large intrinsic charge transport capabilities and optical transparency, may open a new perspective for next-generation (opto)electronics. In the third chapter of this thesis, a series of BTBT-based small molecules, D(C7CO)-BTBT, C7CO-BTBT-CC(CN)2C7, and D(C7CC(CN)2)-BTBT, have been developed in “S-F-BTBT-F-S (F/S: functional group/substituent)” molecular architecture. Combining with D(PhFCO)-BTBT, a molecular library with systematically varied chemical structures has been studied herein for the first time for low LUMO DAcTTs, and key relationships have been elucidated. The molecular engineering perspectives presented in this thesis may give unique insights into the design of novel electron transporting thienoacenes for unconventional optoelectronics.Article Citation - WoS: 54Citation - Scopus: 57Ultralow Bandgap Molecular Semiconductors for Ambient-Stable and Solution-Processable Ambipolar Organic Field-Effect Transistors and Inverters(Royal Soc Chemistry, 2017) Ozdemir, Resul; Choi, Donghee; Ozdemir, Mehmet; Kwon, Guhyun; Kim, Hyekyoung; Sen, Unal; Usta, HakanThe design and development of novel ambipolar semiconductors is very crucial to advance various optoelectronic technologies including organic complementary (CMOS) integrated circuits. Although numerous high-performance ambipolar polymers have been realized to date, small molecules have been unable to provide high ambipolar performance in combination with ambient-stability and solution-processibility. In this study, by implementing highly p-electron deficient, ladder-type IFDK/IFDM acceptor cores with bithiophene donor units in D-A-D pi-architectures, two novel small molecules, 2OD-TTIFDK and 2OD-TTIFDM, were designed, synthesized and characterized in order to achieve ultralow band-gap (1.21-1.65 eV) semiconductors with sufficiently balanced molecular energetics for ambipolarity. The HOMO/LUMO energies of the new semiconductors are found to be -5.47/-3.61 and -5.49/-4.23 eV, respectively. Bottom-gate/top-contact OFETs fabricated via solution-shearing of 2OD-TTIFDM yield perfectly ambient stable ambipolar devices with reasonably balanced electron and hole mobilities of 0.13 cm(2) V-1 s(-1) and 0.01 cm(2) V-1 s(-1), respectively with I-on/I-off ratios of similar to 10(3)-10(4), and 2OD-TTIFDK-based OFETs exhibit ambipolarity under vacuum with highly balanced (mu(e)/mu(h) similar to 2) electron and hole mobilities of 0.02 cm(2) V-1 s(-1) and 0.01 cm(2) V-1 s(-1), respectively with I-on/I-off ratios of similar to 10(5)-10(6). Furthermore, complementary-like inverter circuits were demonstrated with the current ambipolar semiconductors resulting in high voltage gains of up to 80. Our findings clearly indicate that ambient-stability of ambipolar semiconductors is a function of molecular orbital energetics without being directly related to a bulk p-backbone structure. To the best of our knowledge, considering the processing, charge-transport and inverter characteristics, the current semiconductors stand out among the best performing ambipolar small molecules in the OFET and CMOS-like circuit literature. Our results provide an efficient approach in designing ultralow band-gap ambipolar small molecules with good solution-processibility and ambient-stability for various optoelectronic technologies, including CMOS-like integrated circuits.Article Citation - WoS: 61Citation - Scopus: 74Solution-Processable Bodipy-Based Small Molecules for Semiconducting Microfibers in Organic Thin-Film Transistors(Amer Chemical Soc, 2016-05-23) Ozdemir, Mehmet; Choi, Donghee; Kwon, Guhyun; Zorlu, Yunus; Cosut, Bunyemin; Kim, Hyekyoung; Usta, HakanElectron-deficient pi-conjugated small molecules can function as electron-transporting semiconductors in various optoelectronic applications. Despite their unique structural, optical, and electronic properties, the development of BODIPY-based organic semiconductors has lagged behind that of other pi-deficient units. Here, we report the design and synthesis of two novel solution-proccessable BODIPY-based small molecules (BDY-3T-BDY and BDY-4T-BDY) for organic thin-film transistors (OTFTs). The new semiconductors were fully characterized by H-1/C-13 NMR, mass spectrometry, cyclic voltammetry, UV-vis spectroscopy, photoluminescence, differential scanning calorimetry, and thermogravimetric analysis. The single-crystal X-ray diffraction (XRD) characterization of a key intermediate reveals crucial structural properties. Solution-sheared top-contact/bottom-gate OTFTs exhibited electron mobilities up to 0.01 cm(2)/V center dot s and current on/off ratios of >10(8). Film microstructural and morphological characterizations indicate the formation of relatively long (similar to 0.1 mm) and micrometer-sized (1-2 mu m) crystalline fibers for BDY-4T-BDY-based films along the shearing direction. Fiber-alignment-induced charge-transport anisotropy (mu?/mu approximate to 10) was observed, and higher mobilities were achieved when the microfibers were aligned along the conduction channel, which allows for efficient long-range charge-transport between source and drain electrodes. These OTFT performances are the highest reported to date for a BODIPY-based molecular semiconductor, and demonstrate that BODIPY is a promising building block for enabling solution-processed, electron-transporting semiconductor films.Doctoral Thesis Yüksek Performanslı Organik Transistörler ve Güneş Pilleri Uygulamaları için Yeni Yarı İletken Malzemeler(Abdullah Gül Üniversitesi, Fen Bilimleri Enstitüsü, 2022) Can, Ayşe; Usta, HakanIn the first chapter, we review the historical and recent advances in the design and implementation of indenofluorene (IF)-based semiconductors in organic transistor and solar cell devices. In the second chapter, a series of n-type ambient-stable and solution- processable TIFDMT-based semiconducting molecules, β,β'-C8-TIFDMT, β,β'-C12- TIFDMT, and β,β'-C16-TIFDMT are reported. By utilizing alkyl chain engineering in TIFDMT-based molecules and semiconductor-dielectric interface engineering through PS-brush treatment onto the dielectric surface in their OFET devices, we optimize the semiconductors' morphologies and thin-film molecular packing motifs to attain high- performance OFETs. The PS-brush treated OFETs demonstrate high device performance with μe = 0.9 cm2/V.s and Ion/Ioff ratio = 107-108. In the third chapter, we demonstrate the design, synthesis, and characterizations of two novel meso-π-extended/-deficient BODIPY building blocks (2OD-T2BDY and 2OD-TTzBDY), a library of low band gap (Eg = 1.30-1.35 eV) donor-acceptor copolymers based on these building blocks, and the utilization of the D-A copolymers as donor materials in the bulk heterojunction organic photovoltaics. Power conversion efficiencies of up to 4.4% with a short-circuit current of 12.07 mA cm-2 are achieved. The findings of this thesis on molecular engineering and optoelectronic properties are unique and may provide critical insights into the future development of high performance materials for unconventional optoelectronics.Article Citation - WoS: 27Citation - Scopus: 29Revisiting the Role of Charge Transfer in the Emission Properties of Carborane-Fluorophore Systems: A TDDFT Investigation(Amer Chemical Soc, 2022-06-05) Tahaoglu, Duygu; Usta, Hakan; Alkan, FahriIn this study, we performed a detailed investigation of the S-1 potential energy surface (PES) of o-carborane-anthracene (o-CB-Ant) with respect to the C-C bond length on o-CB and the dihedral angle between o-CB and Ant moieties. The effects of different substituents (F, Cl, CN, and OH) on carbon- or boron-substituted o-CB, along with a pi-extended acene-based fluorophore, pentacene, on the nature and energetics of S-1 -> S-0 transitions are evaluated. Our results show the presence of a non-emissive S-1 state with an almost pure charge transfer (CT) character for all systems as a result of significant C-C bond elongation (C-C = 2.50-2.56 angstrom) on o-CB. In the case of unsubstituted o-CB-Ant, the adiabatic energy of this CT state corresponds to the global minimum on the S-1 PES, which suggests that the CT state could be involved in emission quenching. Despite large deformations on the o-CB geometry, predicted energy barriers are quite reasonable (0.3-0.4 eV), and the C-C bond elongation can even occur without a noticeable energy penalty for certain conformations. With substitution, it is shown that the dark CT state becomes even more energetically favorable when the substituent shows -M effects (e.g., -CN), whereas substituents showing +M effects (e.g., -OH) can result in an energy increase for the CT state, especially for partially stretched C-C bond lengths. It is also shown that the relative energy of the CT state on the PES depends strongly on the LUMO level of the fluorophore as this state is found to be energetically less favorable compared to other conformations when anthracene is replaced with pi-extended pentacene. To our knowledge, this study shows a unique example of a detailed theoretical analysis on the PES of the S-1 state in o-CB-fluorophore systems with respect to substituents or fluorophore energy levels. Our findings could guide future experimental work in emissive o-CB-fluorophore systems and their sensing/optoelectronic applications.Article Citation - WoS: 40Citation - Scopus: 40Design, Synthesis, and Characterization of Α,ω-Disubstituted Indeno[1,2-B]Fluorene Molecular Semiconductors. Enhancement of Ambipolar Charge Transport Through Synthetic Tailoring of Alkyl Substituents(Royal Soc Chemistry, 2016) Ozdemir, Mehmet; Choi, Donghee; Kwon, Guhyun; Zorlu, Yunus; Kim, Hyekyoung; Kim, Myung-Gil; Usta, HakanA series of indeno[1,2-b]fluorene-6,12-dione-thiophene derivatives with hydrocarbon substituents at alpha,omega-positions as side groups have been designed and synthesized. The new compounds were fully characterized by H-1/C-13 NMR, mass spectrometry, cyclic voltammetry, UV-vis absorption spectroscopy, differential scanning calorimetry, thermogravimetric analysis, and melting point measurements. The solid state structure of the indeno[1,2-b]fluorene-6,12-dione acceptor core has been identified based on single-crystal X-ray diffraction (XRD). The structural and electronic properties were also studied using density functional theory calculations, which were found to be in excellent agreement with the experimental findings and provided further insight. The detailed effects of alkyl chain size and orientation on the optoelectronic properties, intermolecular cohesive forces, thin-film microstructures, and charge transport performance of the new semiconductors were investigated. Two of the new solution-processable semiconductors, 2EH-TIFDKT and 2OD-TIFDKT, were deposited as thin-films via solution-shearing, drop-casting, and droplet-pinned crystallization methods, and their morphologies and microstructures were investigated by X-ray diffraction (XRD) and atomic force microscopy (AFM). The solution-processed thin-film transistors based on 2EH-TIFDKT and 2OD-TIFDKT showed ambipolar device operations with electron and hole mobilities as high as 0.12 cm(2) V-1 s(-1) and 0.02 cm(2) V-1 s(-1), respectively, with Ion/Ioff ratios of 105 to 106. Here, we demonstrate that rational repositioning of the b-substituents to molecular termini greatly benefits the p-core planarity while maintaining a good solubility, and results in favorable structural and optoelectronic characteristics for more efficient charge-transport in the solid-state. The ambipolar charge carrier mobilities were increased by two-three orders of magnitude in the new indeno[1,2-b]fluorene-6,12-dione-thiophene core on account of the rational side-chain engineering.Article Citation - WoS: 12Citation - Scopus: 11Trans-Cis Isomerization Assisted Synthesis of Solution-Processable Yellow Fluorescent Maleic Anhydrides for White-Light Generation(Elsevier Science SA, 2015-12) Ozdemir, Mehmet; Genc, Sinan; Ozdemir, Resul; Altintas, Yemliha; Citir, Murat; Sen, Unal; Usta, HakanHeterocyclic maleic anhydride derivatives have been extensively studied in natural products chemistry over the past few decades. However, their incorporation into optoelectronic devices has lagged behind that of other pi-conjugated systems, and they have never been studied in white light emitting diodes (WLEDs). The development of emissive pi-conjugated materials for (WLEDs) has been an emerging scientific and technological research area to replace phosphors used in LED-based solid-state lighting. Here, we demonstrate the design, synthesis and characterization of two new highly emissive alkyl-substituted bis(thienyl)maleic anhydrides (C6-Th2MA and C12-Th2MA) with favorable photophysical properties. The new core is synthesized via a novel trans-to-cis isomerization-assisted one-pot reaction, which is demonstrated for the first time in the literature for the synthesis of a bis(heteroaryl)maleic anhydride. Due to its favorable absorption and fluorescence properties in the blue and yellow region of the visible spectrum, respectively, C12-Th2MA is studied as a potential wavelength-upconverting material. A WLED fabricated by drop-casting a polymeric solution of C12-Th2MA on a blue LED (InGaN, 455 nm) yields promising CIE coordinates and color-rendering index (CRI) values of (0.24, 0.20) and 65.0, respectively. Considering the simplicity of the current molecular structure and facile synthesis, alkyl-substituted bis(thienyl)maleic anhydrides stand as ideal phosphor alternatives. Therefore, the current findings may open new perspectives for the development of maleic anhydride-based small molecules for low-cost, energy-efficient, and solution-processed lighting technologies. (C) 2015 Elsevier B.V. All rights reserved.Master Thesis Solüsyondan Proses Edilebilir Çubuk Yapısında Moleküler Yarı İletkenler ve Alan Etkili Transistör Uygulamaları(Abdullah Gül Üniversitesi, 2018) DENEME, İBRAHİM; Deneme, İbrahim; Usta, HakanYeni n-tipi yarı iletkenlerin yapısal dizaynı ve sentetik olarak geliştirilmesi yük taşıma mekanizmasının temellerinin anlaşılması noktasında bilimsel ve teknolojik alanlarda önemli derecede ilgi uyandırmıştır. Son yıllarda literatürde mevcut çok sayıda n-tipi yarı iletken olmasına rağmen, solüsyondan proses edilebilen ve havada kararlı n-tipi yarı-iletken malzeme sayısı oldukça sınırlıdır. Burada biz, indeno[1,2-b]floren ve (triizopropilsilil)etinil tabanlı, 6,12-pozisyonlarında disiyanovinilen ve 2,8-pozisyonlarında ise karbonil fonksiyonel grupları içeren iki yeni moleküler yarı-iletkenlerin dizaynı, sentezi, tek kristal yapıları, optoelektronik özellikleri, çözelti ile proses edilmiş ince-film morfolojilerini/mikroyapılarını ve organik alan etkili transistör uygulamalarını ortaya koyduk. Elektron çekici karbonil, disiyanovinilen ve (triizopropilsilil)etinil gruplarının indeno[1,2-b]floren π-merkezine dahil edilmesi, tamamen akseptör tipinde π-konjuge yapının oluşmasına sebep olmaktadır. Söz konusu yeni moleküller, 2,8- (triizopropilsilil)etinil-indeno[1,2-b]floren-6,12-dion (TIPS-IFDK) ve 2,8-(triizopropilsilil)etinil-indeno[1,2-b]floren-6,12-bis(disiyanoviinilen) (TIPS-IFDM)'dir. Yeni bileşiklerin HOMO/LUMO enerjileri sırasıyla TIPS-IFDK için -5.77 / -3.65 eV ve TIPS-IFDM için -5.84 / -4.18 eV'dir. Daha önce geliştirilen donör-akseptör tipi indenofluorenler ile kıyaslandığında tamamen akseptör yapıda π-konjuge sisteme sahip oldukları için yeni moleküllerin optik bant aralıklarında artış gözlemlenmiştir. (TIPS-IFDK için 2.12 eV ve TIPS-IFDM için 1.66 eV) TIPS-IFDK ve TIPS-IFDM yarı-iletkenlerinin katı-hal düzenlemeleri ve moleküller arası π-π etkileşimleri, tek kristal X-ray difraksiyon (XRD) analizi ile incelenmiştir. Söz konusu yarı-iletkenler katı halde 1-D kolon yapısı ortaya koymuştur. Bu tez kapsamında geliştirilen TIPS-IFDM yarı-iletkeni kullanılarak, solüsyon-makaslama (solution-shearing) yöntemi ile alt kapı/üst temas organik alan etkili transistörler üretilmiştir. Havada son derece kararlı olan söz konusu transistörler n-tipi yük taşıma karakterinde olup, 0.02 cm2/Vs elektron hareketliliği, 107 Ion/Ioff oranı sergilemiştir. Buna rağmen bu tez kapsamında geliştirilen diğer molekül TIPS-IFDK, TIPS-IFDM ile kıyaslandığında 103 kat daha az elektron hareketliliği ortaya koymuştur. Bu durum TIPS-IFDK molekülünün zayıf π-π etkileşimleri ve ince-film fazında zayıf kristal yapısından kaynaklanmaktadır. Dolayısıyla TIPS-IFDK tabanlı OFET'ler havada kararlı değildir. (trialkilsilil)etinil grubunun HOMO/LUMO orbitalleri üzerindeki elektronik etkileri DFT hesaplamaları ile ortaya çıkarıldı. Bildiğimiz kadarıyla, TIPS-IFDM, uzun moleküler eksen (x) boyunca (trialkilsilil) etinil gruplarıyla fonksiyonel hale getirilmiş, çözücüde proses edilebilen, havada kararlı, n-tipi moleküler yarı iletkenlerin ilk örneğidir. Elde ettiğimiz sonuçlar, havada kararlı n-tipi organik alan etkili transistörler ve çeşitli organik optoelektronik teknoloji uygulamaları için kolay sentezlenebilir, solüsyondan proses edilebilir yeni molekülerin nasıl dizayn edileceği noktasında önemli bilgiler vermektedir. Bu alanlarda ilerde yapılacak araştırmalara ışık tutmaktadır.Article Citation - WoS: 104Citation - Scopus: 109Proton Conducting Poly(Vinyl Alcohol) (PVA)/Poly (2-Acrylamido Sulfonic Acid) (PAMPS)/Zeolitic Imidazolate Framework (ZIF) Ternary Composite Membrane(Elsevier, 2016-02) Erkartal, Mustafa; Usta, Hakan; Citir, Murat; Sen, UnalThe design, synthesis and characterization of novel proton exchange membranes (PEMs) are of significant scientific and technological importance for the realization of fuel cells, actuators, and sensors. Here, we demonstrate a novel ternary composite membrane consisting of poly(vinyl alcohol) (PVA), poly (2-acrylamido-2-methylpropane sulfonic acid) (PAMPS), zeolitic imidazolate framework-8 (ZIF-8), which is prepared by physical blending and casting methods. To enhance the water management of the membranes, in situ chemical cross-linking is carried out by glutaraldehyde (GA). During the characterization of the new membranes, FT-IR is used for intermolecular and inter-polymer interactions between different components of the membrane, SEM is used to identify morphology, XRD is used to prove the presence of ZIF-8 nanoparticles, and finally TGA is used for thermal stability. The proton conductivity of the membranes is found to increase with temperature and also with the increasing content of PAMPS. The highest proton conductivity under fully hydrated state at 80 degrees C is measured as 0.134 S cm(-1) for PVA: PAMPS: ZIF-8 (55:40:5) composition. In this study, it is clearly shown that ZIF-8 nanoparticles contribute to the proton conductivity by forming hydrogen bonds with the polymer network in the membrane. The water uptake (WU) and ion exchange capacity (IEC) values are 3.28 (gig) and 1.52 meq g(-1), respectively for the same membrane. To the best our knowledge, this study shows one of the first example of a MOFcontaining membrane with truly high proton conductivities, and both values of proton conductivity and electrochemical properties are comparable to those of well-studied membrane, Nation. (C) 2015 Elsevier B.V. All rights reserved.