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Photophysicochemical Processes Directed Within Nano-Containers

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Dyes and Photoactive Molecules in Microporous Systems

Part of the book series: Structure and Bonding ((STRUCTURE,volume 183))

Abstract

Directing excited-state behavior of photoactive molecules without covalent modification has been more frequently achieved through inclusion within cavitands than by any other supramolecular approach. Such efforts have led to interesting photophysicochemical phenomena and their applications. This includes employing strategies such as use of chromo-/luminophore-cavitand interactions to perturb the electronic states to affect quantum efficiencies of radiative processes or structural pre-orientation of reactants to achieve chemoselectivity. The influence of nano-containers such as macrocyclic cavitands, nanocages, and capsules on the photoactive molecules has been observed in solution phase as well as the solid state, which has been studied through spectroscopy, product selectivity analysis, and computational chemistry. This chapter will highlight prominent works in the past two decades that studied the nano-container-photoactive guest systems whose significance extends well beyond the domain of supramolecular photochemistry. The crucial nature of such works in gaining new insight into electronic, bonding, and dynamics nature of chemical interactions or their role in realizing new applications is discussed herein. The contents are organized on the basis of named photochemical reactions or photophysical activity affected through nano-container mediation contrasted with that of the free chromophore or luminophore. Three cavitands (families) cyclodextrins, cucurbiturils, and octa acids are primarily focused due to their literature predominance leading to a comprehensive understanding of their effects, with relatively less frequent instances of calixarenes and crown-ethers. Differences in physicochemical influences affected by the various cavitand families as well as that within the oligomers of a given family will be discussed wherever possible, and diversity in such effects is analyzed on the basis of “supramolecular cause-and-effect” relationship.

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Abbreviations

α-CD:

α-cyclodextrin

β-CD:

β-cyclodextrin

γ-CD:

γ-cyclodextrin

λfl:

Fluorescence wavelength

τF:

Fluorescence lifetime

Φ:

Quantum yield

ΦF:

Fluorescence quantum yield

ACN:

Acenaphthylene

ADT:

Adamantathione

ANT:

Anthracene

aPS:

Activatable photosensitizers

BP:

Biphenyl bipyridinium guest

CA:

Cinnamic acid

CB:

Cucurbituril

CB7:

Cucurbit[7]uril

CB8:

Cucurbit[8]uril

CD:

Cyclodextrin

CE:

Crystal engineering

CHT:

Camphorthione

Coum-n:

Coumarins

D-A:

Donor-acceptor

DBA:

Dibenzal acetone

DMABN:

N,N-Dimethylaminobenzonitrile

DNC:

Dinaphthyl crown ether

E*:

Excimer

FNT:

Fenchthione

HH:

Head-to-head

HOMO:

Highest occupied molecular orbital

HT:

Head-to-tail

IC:

Internal conversion

ISC:

Intersystem crossing

ITC:

Intramolecular charge transfer

L:

Linker

LE:

Local excited state

LUMO:

Lowest unoccupied molecular orbital

M*:

Excited-state monomer

MM:

Molecular mechanics

MO:

Molecular orbital

NBS:

N-benzyl succinimide

NpE:

Naphthyl benzoates

NPM:

N-phenylmaleimide

OA:

Octa acid

OAm:

Octa amine

P*:

Excited-state product

PAH:

Polyaromatic hydrocarbon

PCA:

Photocycloaddition

Pd-NC:

Palladium nanocage

PDT:

Photodynamic therapy

Py:

Pyrene

R*:

Excited-state reactant

RH:

Rebek’s host

RTP:

Room temperature phosphoroscence

SOG:

Singlet oxygen generator

SQ:

Squaraines

STB:

4,4′-dimethyl stilbene

ST-n:

Stilbazole guests

TB-B:

Biotinylated toluidine blue

TF:

Thioflavin

TICT:

Twisted intramolecular charge transfer

TP+:

2,4,6-triphenylpyrylium

TPOR:

Tetranaphthyl-substituted porphyrin

VSEPR:

Valence shell electron pair repulsion

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Acknowledgments

AN thanks GE Additive to support and approve the publication content. MP would like to thank his professional and life partner, Dr. Surabhi Chandra, for her support and patience during the preparation of this chapter. He also expresses his gratitude to Dr. Richard Mocarski (Assistant Vice Chancellor for Research) for his passionate support for research and providing new opportunities for researchers at UNK.

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  1. Department of Chemistry, University of Nebraska Kearney, Kearney, NE, USA

    Mahesh Pattabiraman

  2. GE Aviation, West Chester, OH, USA

    Arunkumar Natarajan

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Correspondence to Mahesh Pattabiraman .

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  1. Department of Physical Chemistry, University of the Basque Country UPV/EHU, Bilbao, Vizcaya, Spain

    Virginia Martínez-Martínez

  2. Department of Physical Chemistry, University of the Basque Country UPV/EHU, Bilbao, Vizcaya, Spain

    Fernando López Arbeloa

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Pattabiraman, M., Natarajan, A. (2020). Photophysicochemical Processes Directed Within Nano-Containers. In: Martínez-Martínez, V., López Arbeloa, F. (eds) Dyes and Photoactive Molecules in Microporous Systems. Structure and Bonding, vol 183. Springer, Cham. https://doi.org/10.1007/430_2020_64

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